Category Archives: Michael Pickering

In the News: Phthalates

By Michael Pickering

While reading the NY Times one morning in March, I came across an article titled “A Plastic Threat to Male Fertility” in the Science Times section. Having encountered phthalates in the past, I was curious to read further.

Federal researchers recently spent four years tracking 501 couples who were trying to have children. The goal of their study was to assess the impact of everyday chemicals on fertility. While both men and women were exposed to known toxins, men appeared much more likely to suffer fertility problems as a result.

“Anything you can think of that’s testosterone-dependent is likely to be affected.”   – Heather Patisaul, North Carolina State University

The gender disparity was most significant when it came to phthalates. This group of petrochemicals finds its way into many commercial products. Phthalates are among a group of compounds known as endocrine disruptors. As the endocrine system controls the production and distribution of hormones in the body, they have been implicated in a range of health problems. Unlike many of the study’s other industrial toxins that bio-accumulate, phthalates are metabolized within hours of ingestion. However, their pervasiveness in the environment means almost constant exposure, which increases their impact.

Among the myriad uses for phthalates are as plasticizers (rendering polymers flexible rather than brittle) and in cosmetics, where they improve smoothness of flow upon application.

Partial List:

  • Cosmetics
  • Plastics
  • Household products
  • PVC pipes
  • Hospital tubing
  • Medicine (pills, capsules)
  • Air filters, residential and commercial

While the evidence for an effect on male fertility is compelling, it is still difficult for researchers to gauge the full impact these prevalent phthalates are having. If you want to minimize your exposure, read labels, do not heat anything you intend to ingest in plastic, and bring your own glass to the keg party.

IN THE PAST: Phthalate Blues

Personally, my formal introduction to phthalates was when I quit teaching high school and went to grad school. My research involved isolating and characterizing secondary metabolites in the plant family Rutaceae. The process involved solvent extraction (soxhlet) and evaporation followed by gravitational silica column chromatography. We learned quickly that all the bulk silica, most of the solvents, and the most popular clear flexible tubing (Tygon) all contained di-octylphthalate (DOP), an oil. The air in the building was also loaded with DOP due to the filters. Fortunately, it was easy to keep track of DOP because of its blue fluorescence. The low polarity of the plasticizer made it easy to elute off of the columns with the slurry solvent. For our 20cm x 20cm x 1-2mm thick layer prep plates, we formed and dried them, and then placed them in the chromatography chamber with acetone. Upon re-drying, the plates viewed under UV light were flat white with a bright blue edge along the top.

Most of my targeted metabolites are fluorescent; yellow, green, pink, and blue to the eye. I once inadvertently isolated a non-chromophoric terpene because I was chasing an indigo blue fluorescent spot on the TLC. Upon elution from the plate, I got an oil. Mass spectrometric analysis revealed the terpene in a tableau of DOP fragments. The friend who ran the mass spec for me, Charlie, was in charge of a spectroscopy lab for a veterinary toxicology department at the time. He said he could recognize all the spectrographic manifestations of DOP from twenty paces.

My last encounter with DOP was several years later, in a Pickering customer’s lab. An extremely agitated gentleman had called to announce that he had “NO PEAKS!!!” So, our customer service chemist went for a visit, and I went along for the ride.

We arrived at 10:00am, and fortunately the system was running. He had a Carbamate post-column instrument paired with a water/methanol two-pump, four-piston binary gradient HPLC. The pistons were ganged in series. Our chemist engaged the customer while I observed the instrument. The fluorometer was so overloaded with signal that the PM tube was regularly turning off. There was no troubleshooting information available from the magnitude of the signal, but there was a very regular and periodic spike, implying a piston cycle.

Upon further observation of the HPLC, I noticed that both reservoirs’ contents had traveled up into the Nitrogen lines and was sloshing around in the Tygon tubing. With this back-flowed solution being sloshed back into the reservoir periodically, I realized the problem. Although Tygon tubing is phthalate-free today, it was loaded with DOP back then. The swamping fluorescence was in both reservoirs. The spike frequency was the last piston on the methanol pump, where the DOP concentration would be the highest.

The customer had his peaks, he just couldn’t see them for the bright lights.

Chromatography Quiz #16

Chromatography Quiz #15 Results

We would like to congratulate our grand prize winners of our last newsletter’s Amino Acids Analysis Chromatography Quiz: Tom Schneider from Suffolk County Water Authority, Jim Balk from DHHS Public Health Environmental Laboratory, and Narjes Ghafoori from LA County Environmental Toxicology Laboratory!

They have each won and will shortly be receiving: a $100 gift card for Best Buy, which can be used online or in the store!!!

We would like to thank all of you for your submissions!

The correct answer for the Amino Acids troubleshooting chromatogram: the baseline noise was caused by a dirty flow cell. As we have seen through several Chromatography Quizzes, baseline noise can have a variety of causes, both mechanical and chemical. In this chromatogram, the noise we are seeing is not regular or repeatable, steering us away from the HPLC pump, a trapped bubble, or the back-pressure regulator.

To learn more about baseline noise, please review Maria’s article entitled “The Art of Noise” (http://pickeringlabs-retentiontimes.com/?p=58) from a previous newsletter.

Thank you!

Pickering Labs

Chromatography Quiz #16:

We are doing something a little bit different with this quiz! Identify what’s wrong with the picture below and win a prize! Simply email your answer as well as your full contact information to Rebecca at rlsmith@pickeringlabs.com by July 1st, 2014 in order to win. You will receive email confirmation that your submission has been received. The answer to the quiz and winner congratulations will be published in the next issue (to be anonymous, please notify Rebecca in your submission).

A blast from the past: What is wrong with this picture?!

As you can probably tell from the photo, we’ve dug into Michael’s past for our quiz this quarter! Look carefully and see if you can figure out what’s wrong with this picture! If you have any questions, please feel free to email Rebecca at rlsmith@pickeringlabs.com for further guidance.

Michael_Trione Ad

A Story with Bearing: Cholesterol

A Story with Bearing: Cholesterol

By Michael Pickering

Years ago our friend Peggy told us that her doctor had prescribed a diet devoid in cholesterol, as her blood test indicated worrisome numbers.  The doctor recommended that all of the usual suspects be excluded from her diet, such as egg yolks and butter, but it was all to no avail.  Regardless of how long she maintained the exclusive diet, her blood numbers did not budge.  So, she decided to experiment with her own dietary exclusions.  One of her first experiments was targeted at a food everyone who knows Peggy is well aware that she is addicted to – milk chocolate.  It was only then that her blood cholesterol numbers improved.

While it is true that one’s diet is an important factor in the level of cholesterol in one’s blood, the amount of cholesterol in one’s diet is not germane.  Unlike the essential amino acids and minerals which must be harvested from the diet, the cholesterol in our blood is synthesized inside our bodies from smaller synthons (many acetates, a popular biosynthetic mode, see flavonoids).

So the issue isn’t whether cholesterol is in one’s diet, but rather how cholesterol is behaving in one’s blood.

The key link between the importance of diet and the behavior of cholesterol in one’s blood is the amount and type of fat you ingest.  Highly saturated fats have the most negative impact on the solubility of cholesterol in the blood.

mink coat front

Blood chemistry is necessarily dominated by water soluble processes.  Magnesium, sodium, citrate, and all manner of water soluble nutrients must course around freely.  However, cholesterol is not water soluble, even though it must move as freely through our veins.  The body’s solution is to cloak the cholesterol with a hydrophobic interior (cozy coat) with a hydrophilic exterior (sort of like a 1960’s Bill Blass coat with the mink on the inside and the satin on the outside).mink coat back

These water taxis are called LDL and HDL: low density lipoproteins and high density lipoproteins.  Our body considers the HDL to be better than the LDL because, among other things, it’s easier to void.   Tom Scheve’s description of the reason for this in his article for Discovery Health, entitled “What’s the difference between LDL and HDL Cholesterol” eloquently expresses my own musings:

When the lipoprotein has more protein than cholesterol [HDL], it resembles a Ferrari, gunning through your body without stopping until the cholesterol arrives at your liver, where it’s converted into bile acids.  […]  When the lipoprotein has more cholesterol than protein [LDL], however, this makes for a rickety    ride, and that jalopy doesn’t get too far.  Cells have special receptors that bind tightly to these lipoproteins as they pass.  This LDL sputters down the road, careening off the arteries, running into things and leaving bits all over the place.  While the HDL Ferrari sees a pileup and nimbly speeds around it, the LDL jalopy crashes right into it, adding to the jumble of tangled fenders and tailpipes (or platelets and plaque).

The overall solubility of cholesterol in the blood is governed by a ternary phase diagram. ternary phase diagramMaintaining these three components in the proper ratio crates a zone of solubility in the triangle.  If the diet (the source of phospholipids and fats) biases the ratio out of the soluble zone, the cholesterol precipitates with the fenders and tailpipes.  And like all solids in a moving fluid, they deposit in the zones of slowest flow.  In a vascular system the slowest flow is in the arteries.

The lipids (fats) in our diet can be broadly sorted into two categories: 1) naturally occurring, and 2) man-made.  Obviously the naturally occurring fats and oils are derived from plants and animals.  The man-made fats are partially hydrogenated vegetable oils.  The saturation level determines the melting point and viscosity regardless of the source.  So highly unsaturated lipids like sesame oil have a low melting point and viscosity and so are inappropriate for frying, whereas poly-saturated lard and butter have a high melting point and viscosity, and are well suited for frying.  Similarly, an award-winning pie crust can be made with lard or butter, but not with unsaturated oil.  Partial hydrogenation thus controls the melting point of the fat and establishes its suitability for any particular application.

However, a side reaction also occurs during the hydrogenation: isomerization.  Natural unsaturation tends to be cis-configuration but hydrogenation isomerizes the bonds to trans-configuration.

cis trans fat structuresWhile the hydrogenation controls the melting point precisely (which is essential for processed foods), the resulting fat is not recognized by the body as food.

Our wild type diet is clearly designed around whole grains as the staple, a source uniquely rich in unsaturated (cis-) fats, phospholipids, and protein.  The goal is to manage the trace chemistry in our blood, the hydrophobic components.  So the lesson is: eat as little saturated (mostly animal) fat as you can tolerate, eat whole grains and exclude all partially hydrogenated vegetable oil.  Read the label!

So while the amount of cholesterol present in a milk chocolate bar (24 g) is comparable to that of a tablespoon of butter (30 g), the two had very different effects on Peggy’s blood work.  Cocoa fat is among the most saturated of the vegetable oils.  The melting point is so high that the bars are wax-like at room temperature.  The chocolate was in effect creating an excess of LDL jalopy wreckage in Peggy’s blood stream, by causing the LDL and HDL levels to get out of whack.

The cholesterol had no bearing.

 

Editor’s Note: Always consult a physician first. The views presented herein are strictly editorial in nature.

Caltrans, the Blunder Lizard

By Michael Pickering

The largest known dinosaur was the Brontosaurus, literally the thunder lizard.  Its brain, estimated as the size of a fist, was too small to manage the whole beast. Apatozaur, Apatosaurus, Brontozaur, Brontosaurus, DinoAnimals.pl, Portal.DobreSciagi.pl Instead, it used a distributed intelligence in the form of neuro-bodies called ganglia.  Since they had only one neural system, the decision nodes were in constant, real-time communication.  This form of committee decision is the initial model for Caltrans management.  However, unlike the dinosaur, Caltrans adds an orthogonal system of decision node ganglia.  Not only is there a multiplicity of decision nodes within Caltrans, but other state agencies are nodes as well.  The dinosaur’s decisions were planar while Caltrans is a volume, both horizontal and vertical.

In the last century, during my early teens, perhaps middle or high school, I heard a Q/A joke:

Q:  What’s orange and sleeps four?

A:  A Caltrans van.

Caltrans was founded in 1895 as the Bureau of Highway.  Today it owns and operates ~15,000 miles of the California State Highway System.  Its annual budget is in excess of six billion dollars and it has more than 20,000 employees.

Because of the amount of public moneys involved and the scale of their projects, Caltrans regularly makes front-page news.  Unfortunately, it is always bad ink: delivery deadlines missed by years, budget overruns by many zeros.

In 1993, in order to address these common failures, Caltrans Director Van Loben Sels issued a charter to hold a peer review of the project management implementation plan.  The study group included Bechtel Corp., the U.S. Corps of Engineers, and the US Department of the Navy.  Some of their findings include the lack of:

  • realistic goals and objectives linked to civil service constraints;
  • communication, with specific roles and responsibilities not uniformly understood;
  • consistent management support with different district agendas; and
  • authority, with micromanagement by headquarters.

Similarly, in 1994 SRI International evaluated project management in response to Senate Concurrent Resolution No. 72.

bay bridge new span 2013
Eastern Span of Bay Bridge in 2013
Photo: Michael Macor, The SF Chronicle

The study found that Caltrans remains “rule driven” rather than “product driven” due to its longstanding bureaucratic culture.  SRI concluded that the Caltrans culture, not the organizational structure, was the culprit.  At the time, news analysts across the state described the audit as “scathing.”

So here we are in June of 2013.  Caltrans is front-page news because the replacement Bay Bridge span is years overdue and seriously over budget.  (Does anybody even remember that the reason for building the new span is that the old span is damaged and unsafe?).  The headlines are “Who Picked the Bad Bolts?”  The federal government is investigating California, the California legislature is investigating Caltrans, Caltrans is investigating vendors and other State agencies, and vendors are professing that all products were produced to the ordered specifications.  Although the bolts were made to spec (we hope; the jury is still out on this point), using them in this particular bridge design was inappropriate.

Eastern Span of Bay Bridge 2005
Photo: Wendy Rasmussen

The news reports of the multiplicity of investigations will drift off of the front page.  No little brain will be found, no ganglia identified.  Nothing will be revealed in real time.  The volume of decision nodes will hide all culpability.  The last report will be silence.

 

 

Editor’s Note:

The dinosaur which many of us know as Brontosaurus never really existed. The paleontologist who assembled the beast mistakenly placed the head of camarasaurus on the body of an apatosaurus. NPR has a fun story on this topic: http://www.npr.org/2012/12/09/166665795/forget-extinct-the-brontosaurus-never-even-existed

So does the UnMuseum  http://www.unmuseum.org/dinobront.htm

 

Images:

http://dinoanimals.pl/wp-content/uploads/2013/02/Apatozaur-Apatosaurus-Brontozaur-Brontosaurus-1.jpg

http://commons.wikimedia.org/wiki/File:Pasta-Brontosaurus.jpg

http://www.sfgate.com/bayarea/article/Broken-bolts-may-delay-Bay-Bridge-opening-4390299.php#photo-4385726

Believe it or Not

Believe it or Not

By Michael Pickering

Praying_Mantis_Mating_European-30
Praying Mantis

As a culture, we are obsessed with bugs.  We view all bugs, insects, beetles, and especially spiders as being nefarious.  The only general exceptions that come to mind are butterflies and ladybugs.  Even people who do not know the diet of the larvae and the beetles think they are cute.  But in this world view, the bug daddy of all of our fears is bacteria.  With the constant reminder of bacteria-contaminated food recalls and drug-resistant bacteria, we freak out.  Fungus is relegated to a minor role because most people think it only infects milk, cheese, and bread where the result is unsavory but not dangerous.  If your feet itch or you have a yeast infection, you consider it a treatable nuisance.

This is a skewed thought balance.  The crawly, multi-legged creatures fall into several categories: pernicious (usually economic damage), beneficial (usually predators of the former), symbiotic, etc.  One of the least populated categories is dangerous.  Similarly, most bacteria are benign or beneficial.  The rare, dangerous bacteria are mostly selected for by our overuse of antibiotics in medicine and more importantly in animal husbandry, where a pound is used for every gram used in medicine.  The devastation caused by fungus is mostly known to farmers, ranchers, and premature neonates, where it is the leading cause of death.

roach fossil
Cockroaches have been around for millions of years. Image from www.fossilmuseum.com

We despise flies, maggots, and cockroaches.  Cockroach larvae would also be reviled and feared, if ever seen.  This abhorrence is based on the notion that they spread germs.  Everyone knows that flies land on poop and on rotting things where maggots are subsequently found, and that cockroaches come from sewers.  They are very germy, very fungal places indeed.  However, that is exactly why the fly spends ground time where it does, and why the roach travels in sewers.  They and their larvae’s principal diet consists of bacteria and fungi.  Just as pigs to truffles, flies and roaches are attracted by smells.  Because the bacteria and fungi spores arrive airborne, they arrive long before the scent attracts the predators, so their colonies are well-established.

Flies lay eggs on rotting things for the abundance of food available for their larvae.  Not the fruit or vegetation, nor the poop, but the bugs feeding on the substrate.  Flies and roaches don’t transport germs, they eat them.  Aside:  With high sugar vegetation such as fruit, the fungus also causes fermentation, making ethanol.  Fruit flies that have been attacked by a wasp have been observed to self-medicate by moving to a “higher proof” fruit, because the wasp larvae implanted in them cannot tolerate the alcohol as well as the flies, thus killing the majority of the intruders.

Bacteria yet remain the scariest to us.  We are so phobic that we try to sterilize everything, including our mouths, our skin, our dwellings and especially our hospitals.  The truth is that we need bacteria to be healthy.  The biome needs bacteria to exist.  The reason hospital bacteria are so virulent and life-threatening is because the antibiotic cleaning agents we use kill 99% of the germs.  The one percent is the territory of the resistant bacteria.  The price the drug resistant bacteria pay for that property renders them non-competitive with the wild-type.  Without the 99% around, they can proliferate.  Aside:  That’s why, when you have a bacterial infection, the doctor insists that you take ALL of the pills.  Most of the unpleasant symptoms are gone after one or two pills, yet you still have a jar of pills.  The doctor is taking care of the one-percenters, the “hells angels” too.

Our mouths, intestines and skin would be dysfunctional were it not for our unique bacterial symbiotes.  Perhaps you have heard the popular parlor question, “what is the germiest part of the human body?”  Most people guess the nether regions, like the anus, or the feet.  In fact, it is the mouth.  Unheard of new strains of bacteria are yet being discovered in the human mouth.  Although healthy urine is sterile, a large part of normal stool is composed of living and dead bacteria.  Manure is always involved in produce recalls due to the presence of dangerous E. coli.  The most difficult type of “food” poisoning to remedy are the ones caused by bacterial invaders that displace the symbiotes in our lower intestine.  Eccrine sweat, which the body produces to regulate temperature and is most abundantly produced on the palms/soles and scalp, includes an antibiotic peptide that protects the resident bacteria.  So it is my opinion that we should use bactericidal cleaning agents sparingly and judiciously.  Don’t use antibacterial mouth washes daily – just when you have an infection like swollen gums or a sore on your cheek.  Do not try to sterilize your skin – use mild, high-fat soap when washing hands and bathing.  Our skin is hydrophobic; don’t make it dysfunctional with strong cleansers and detergents.  I believe that a large percentage of body odor issues and general skin health problems are created by misguided, overly-aggressive cleaning practices and bactericidal-spiked deodorants.

Back to cockroaches, whose presence I think make cities habitable.  Besides micromanaging the microbes in our cities, they are a balanced, healthy diet for mammals and so are a popular food in many parts of the world.  Rats and domestic cats find them irresistible too.  I’m reminded of a conversation with a visitor to our booth at the Pittsburg Conference one year.  He introduced himself as the “head shit chemist” of his state and city.  He mused about why he wasted state money on buying sophisticated, expensive air monitoring equipment for his sewer workers.  The workers had an inviolate rule about entering sewers, no matter what the expensive device reported about the quality of the air – no roaches = no entry!

maggots
Photo Credit: Cory Doctorow

Maggots are also beneficial.  Their merits have been praised in the medical literature as far back as the Greek physician Galen, during wars and for the victims in serious accidents involving exposed wounds.  An exposed wound on an immobile person is an ideal host for bacteria and fungi.  The flies eventually arrive, delivering the maggot “maids” who clean the wound, including the dead flesh, and leave the healthy parts intact.  Their metabolic heat helps to keep the patient warm if exposed to cold weather.  When I was in high school, there was an article in the LA Times about a lady who had plunged into a canyon in the Angeles Crest Mountains during winter and was not discovered for several days.  She was pinned in the car and had serious lacerations on her face, as her head had broken the door window.  Her survival was attributed to the maggots on her face – no germs or rotting flesh present, and enough heat generated to prevent hypothermia.

When observing nature, your senses, your beliefs and your emotions are all involved.  Adjust your dials accordingly.

Ripley did not care whether his writers’ submissions were true or not.  They just had to “sound good, ring true.”

Believe it or not.

The Great One

-By Michael Pickering

One tour of Denali National Park is a bus ride on a dirt and stone road.  The buses are old but so well designed that they are easy to maintain in good working order and well suited to the motorway.  The motorway is in itself a thing of beauty and wonder.  A notch on the flank of a mountain that persists, with some hand maintenance, intact in spite of the onslaught of enormous amounts of erosive rain, snow, and wind.  It is a day replete with photo opportunities, epic vistas, glaciers disguised as mountains, wildlife and flowers, and the lore of Alaska.

Denali Alaska State Flower – the Forget Me Not

When anyone on the bus sees a critter they yell out and the tour guide/bus driver stops and adjusts the position so that all who want a photo can get a good shot.  The grizzlies are much smaller than the famous Kodiaks, as they eat little meat.  They are also blonde, not dark brown, so they are easy to spot at a distance.

Grizzly Crossing Grizzly Bear and her cubs

Denali is the indigenes’ name for Mount McKinley.  It was and is formed by a rising granite pluton that is still growing.  His wife, Mount Foraker, was similarly formed.  All the posters of Mt. McKinley on display had the named taped over and the handwritten DENALI in its place.

Denali National Park and Preserve Denali

When the old world migrants traveled across the land bridge to Alaska, they encountered two main tribes and their languages.  The descendants of these peoples in the lower 48 states are Apaches and Navahos, as evidenced by custom and vocabulary.  Native Alaskans call themselves “sourdoughs,” although all those that I met did not know the origin of the term.  Being a Californian, I of course informed them.  Non-natives can achieve “sourdoughness” by staying for three to four years.  It is sort of a tenure track.  To a person, they are Alaskan.  We, the other 49, are America.  The sourdoughs like to tease Texans (who doesn’t?) by telling them that if Alaska was cut in half, Texas would be the third largest state.  They are also welcoming and generous.  One sensed my interest in plants and spontaneously gave me a recipe for a hypoallergenic flower infusion called “homesteaders honey.”  Of course I will.  

The grandeur of Alaska is enough to draw worldwide tourism, as the languages spoken on our train ride and bus tour can attest.  For us, however, it was our first opportunity to visit our daughter, son-in-law, and grandchildren, who had moved to Anchorage a year earlier.  The train ride across the state and bus tour in the park were our mutual amusement. 

Me (left) and the family Mt. Eielson

The title of this column is “Random Tangents.”  It was assigned to me by the editor, Wendy.  The “T” part I get; I regularly spout them during discussions.  To me, the “T’s” are perfectly germane.  The “R’s” are different though.  The “R” part I suspect is a kindness.  I think it’s the editor cutting me some slack.  So it isn’t a job, like a 500 word essay an assigned topic; an opportunity to be creative and/or amusing.

RANDOM: The eight hour train ride from Anchorage to Fairbanks is lined with antique telephone poles.  Most of the glass insulators, predominantly blue, are still in place.  For that matter, so is much of the wiring. 

TANGENT: It intercepted me ¾ of the way into the bus tour.  The topic was about the cyclic relationship between the snowshoe hares and the bobcats.  They are locked in an approximately seven year cycle of too many and too few.  Those studying the relationship are looking for a correlation factor.  One theory is that it is related to sunshine.  Sun spot/flare activity has a seven year cycle.  I suspect something more prosaic.  The hares preferred food is Willow outer bark.  Willow is the most common bush in the lowlands.  The decline in the hare population is caused by an increasing amount of salicylic acid ingestion.  It weakens the hare, causing attrition and sickens the bobcats alike.

Since the salicylic acid is synthesized only in the inner bark, the Cambrian layer, perhaps the hares engineer their own decline.  After denuding the environment of outer bark, only inner bark is available for forage.  Maybe, exposed to the sun, the Cambrian produces excessive salicylic acid, accelerating the die-off.

 

 

Chance Favors the Prepared Mind

“Chance Favors the Prepared Mind” – Louis Pasteur
by Michael Pickering 
Chapter One: Preparation
My father and his four brothers were auto/diesel mechanics.  All the families, including grandma and grandpa, moved to Moorpark, CA during World War II. It’s a small agricultural suburb east of Ventura. Small in this context means few paved roads.  The move occurred when I was about two years old.  Probably just after my brother, who was 23 months younger than me, was born.  
They obtained a property on US Highway 101 in Ventura.  The site had three commercial venues: the “Red Ball Café,” a gas station, and a multi-bay garage with a hydraulic lift.  The men managed the auto business and the women saw to the restaurant.  Grandpa was the gofer and I was his shotgun.  Anyone alive today who ate at the Red Ball during that time will have more than one fond memory. 
By the time I was five, properly greasing a wheel bearing and installing it was something I knew how to do by feel, and how to set the cotter pin.  What I learned is that it is extremelyimportant to expel ALL the air pockets before installation.  It didn’t make any sense to me then, but what five year old is going to doubt a team of mechanics.  Moreover, his father and uncles.  Now that I’m the mechanic, I get it: it’s a concept of Chaos Theory.  (See Figure X)
Figure X: A ball bearing from an improperly lubed auto front wheel.  The balls contact the tapered spindle on the inside (attached to the car) and a wheel race pressed into the drum.  All the balls from this wheel looked like this.  The outer race in the drum looked like a choppy sea, yet the spindle was unmarked.  The air bubbles and the ball orientation were maintained in perfect symmetry by chaos. 
Chapter Two: Chance
By the time I was in middle school, we lived in Highland Park, a small town on the first freeway on Earth – the Pasadena.  Freeways then didn’t have numbers; they were named for their termini (the Santa Anna, the San Bernardino, the Harbor, etc.).  We were the penultimate town before the freeway ended at a light signal in Pasadena at Orange Grove Blvd.  
The boulevard through Highland Park is the world famous Figueroa.  Town was about two miles from our neighborhood and a gradual rise most of the way to the movie theater. Since the movies changed once a week, that was our minimum number of journeys.  There were, however, more trips than that in the summer, because the public pool was further up Figueroa.  
Exiting the movies one day, someone, probably me, suggested that we have a coasting contest.  The rules were simple: one could peddle as much as possible to cross street A, about ¼ mile of the course, then not at all to the finish line at cross street B.  Joe McNeil won the first race, and I took second.  
Well, I decided that if I wanted to win, I’d have to beat Joe.  So I began to think of ways to create an advantage.  After all, we all had three speed (hub) bikes, called English racing bikes at the time. (See Figure Y)  When I realized the race was mostly coasting, I also knew the solution was to reduce friction.  Then I remembered hand packing wheel bearings, which is where I started the project.  I removed and replaced all the bearings, including the pedal hub.  Included in the soup-up job was the most expensive waterproof lube I could find.  It felt more like hand lotion than grease.  While I was preparing the bearings, my mind drifted to other ways to lower friction.  It came to me as an epiphany: any wobble of the wheels would cause friction on the bearings and on the road surface.  
Figure Y: A 1953 Schwinn three speed bicycle.
Although my only thoughts about spokes until then had been to keep clothing and body parts out of them, I had changed enough flat tires to know that they were attached to a threaded nut anchored on the OD side of the rim, and the spoke exit on the ID of the rim was a tension adjustment nut.  So it was back to the bike store to buy a new tool.
My first guess was to tune all the spokes to the same audio frequency.  Since I had no way of knowing the true frequency, my second guess was to pick the highest frequency or tightest spoke.  It also simplified the task to require only tightening.  A jig was prepared in the backyard with two 2 x 4’s so the wheels could be levelly mounted and spun.  The spokes were plucked to find the highest frequency, whereupon all spokes were tuned to match.  When done, the rim (as viewed rotating in the jig from a planar angle, perpendicular to the axle) was ‘S’ shaped.  So, Plan B was hatched. 
 
True flatness had to be established by reference to a fixed point.  Another stick with a horizontal nail through it as a palp or feeler was driven into the ground.  The spokes are anchored in turn on opposite sides of the rim.  As the rim turned, it drifted away or toward the feeler gauge.  So the process was: loosen one spoke, and tighten the next.  The eventual result was two true rims. 
Keeping my head down near the handle bar and centered over the quill, to lower friction even more, I never lost another race.