IT'S ELEMENTAL! uate and postdoctoral research—P205 to dry solvents and Wittig reagents to synthesize olefins. Imagine: nine years of advanced education and training with five years of specialization in organic chemC. DALE POULTER, UNIVERSITY OF UTAH istry—the chemistry of compounds from living organisms—and virtually no mention HOSPHORUS, AN ELEMENT OF PHOSPHORUS AT A GLANCE of phosphorus. tremendous importance in commerce and research, wasfirstisoI was reintroduced to phosphorus by Name*. From the Greek phosphoros, lated by Hennig Brandt in 1669. Hans Rilling, a biochemist at the Universibringer of light, Following the standard practice ty of Utah, when we began a long, producAtomic mass: 30.97. of alchemists of his era, he protected his tive collaboration to study the mechanisms History: Discovered in 1669 by German invention as a "trade secret" in hopes that of the reactions used by nature to join isophysician Hennig Brandt, he had discovered the Philosopher's Stone. prene units. The substrates for our enzymes Occurrence: Widely distributed in Brandt's monopoly was broken a decade were diphosphate esters—molecules beaumany minerals. Phosphate rock, conlater by Robert Boyle, oftenregarded as the tifully designed to be stable at physiologitaining apatite, is an important source. father of chemistry for his insistence on cal pH, but easily activated once inside the Appearance: Solid nonmetat. Ordinary publishing experiments in sufficient detail active site of an enzyme. One of the first phosphorus is a waxy white solid, so they could be reproduced by others. The hurdles I faced was how to prepare subPhosphorus has white, red, and black description that Boyle and his assistant strate analogs for mechanistic studies from attotropes. White phosphorus is soft, Abrose Godfrey Hanckwitz gave to the precious, lovingly synthesized alcohols. The white red phosphorus is powdery. Royal Society of London is a fascinating reactions used then gave miserable yields of Behavior: White phosphorus catches account of their research with phosphorus. at most a few milligrams of product. Over fire spontaneously in air. When exposed It begins with 'As is before shewed, take the next several years, my students and I to damp air, it glows in the dark in a Urine well putrefied in alub" and concludes developed a practical solution based on a process known as chemiluminescence. with "If the Privy Parts be therewith rubsimple displacement using inorganic pyIt reacts vigorously with all the halogens. b'd, they will be inflamed and burning for a rophosphate. We published a detailed deUses: An essential component of tiving good while after." I wonder who volunscription of the procedure in Organic Synsystems found in nervous tissue, teered for that experiment! theses over the objections of a member of bones, cell protoplasm, and DNA, the editorial board who regarded our use mostly as phosphate. Compounds are I was introduced to the wonders ofphosof a vortex mixer, lyophilization, and chroalso used in fertilizers, insecticides, phorus at the tender age of three. This was matography on cellulose to purify the nondetergents, and foods* near the end of World War II, when Mom volatile water-soluble products as being "too and I were living with my grandmother and three aunts, one of whom I convinced to important component in an unrelated set unfamiliar and biochemical" for organic give me a few kitchen matches. My com- of experiments to develop a concoction I chemists. Since then, my organic colleagues bustion experiment soon got out of con- called "chemical dogfood."Numerous for- have become much less hydrophobic. Over the years, my group has become trol, and I spent the next hour or so at the mulations, most of which featured coffee increasingly dependent on phosfront window of my grandmother's house groundsfloatingon a highly colphorus. In addition to the isonervously watching firemen fight a grass ored liquid, were prepared from prenoid diphosphates, we rely fire in thefieldacross the street. At the same as many different ingredients as heavily on recombinant DNA time, phosphate, from Coca-Cola, was an I could find in the kitchen. The technology Consider a few ofthe consumer evaluations I conbeauties of phosphate esters in ducted with my grandmother's this regard: reverse transcription dog Mitzi were negative, and I for making cDNA libraries eventually dropped the project. from RNA, polymerase chain reTHIS ELEMENT In grade school, my research action for synthesizing cusBROUGHT activities became more organtomized DNA, cutting and pastTO YOU BY ized. Several ofmy playmates and ing of DNA to make templates DIVERSA I formed a "chemistry club." We for generating recombinant procombined our chemistry sets and set up a laboratory under the front porch teins, chemical synthesis ofDNA, and highthroughput DNAsequencing. These "tools of my house—I don't think Mom and Dad ever knew about it. By and large our ex- of the trade" for today's chemist studying periments, many of which were more ad- biosynthesis were unimaginable only three vanced versions of the earlier combustion decades ago when I entered the field.
PHOSPHORUS
P
MAGICAL Joseph Wright's "The Alchemist in Search of the Philosopher's Stone Discovers Phosphorus." 58
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study, were successful. We had fun, actually taught ourselves some chemistry and survived with no permanent injuries. The house survived as well! I didn't learn very much about phosphorus in college or in graduate school. Phosphorus played a minor role in my grad-
C. Dale PouiXer is the John A. Widtsoe Distinguished Professor of Chemistry at the University of Utah He has received the ACS Ernest Guenther and Repligen Awards for his work on isoprenoid biosynthesis and is editor-in-chiefof the Journal of Organic Chemistry HTTP://WWW.CEN-0NLINE.ORG
