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The solid-phase synthesis of a polypeptide is described in Fig. 9-3. Chloromethylated polystyrene (usually based on 1% DVB) is commonly used as the polymer support. Reactions are carried out in nonaqueous media, usually methylene chloride, although DMF has also been used. The rst amino acid monomer (often referred to as a unit or residue) is attached to the polymer support by nucleophilic displacement of the benzylic chloride by carboxylate anion. Reasonable reaction rates are achieved by having high concentrations of the carboxylate anion present by using either the cesium or trialkyl ammonium salt instead of the carboxylic acid. The attachment of the rst amino acid to the polymer support also serves the purpose of protecting the carboxyl group. The amino group of the amino acid must be protected (often referred to as N-blocking or N-protecting) to prevent self-condensation of that monomer during attachment to the support. A variety of protecting groups were studied, including carbobenzoxy, p-toluene sulfonyl, triphenylmethyl, and t-butoxycarbonyl. The

t-butoxycarbonyl group (referred to as Boc) is usually formed by reacting the amino acid with 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile. Di-t-butyl dicarbonate and t-butoxycarbonyl azide have also been used for synthesizing Boc-protected amino acids. The Boc

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Bending through a Potentiometer FIGURE A-4: Any time you discover a nice bend with your bending probe, remember that that bend might be variable if you send that connection through a potentiometer. There is no set potentiometer value to try here. Large value pots (above 1M) may be too coarse in their resistance change for a bend that needs only a slight resistance change to shine. On the other hand, a small value pot (5K or less) might not present enough change in resistance to alter the bend to the degree needed. I usually begin with a 1M potentiometer. If the bent response cuts off near the bottom (low resistance) of the pot s range, I know I need a pot with a smaller resistance value (like a 10K). If I turn the pot to full resistance and the bent effect is still changing nicely, I try a pot with a larger value (like a 10M). The switch in the diagram allows the potentiometer bend to be turned on or off, as usual.

9-74

for the dollar abroad Investors looking to the lessons of the past staged a flight from dollars to property and from bonds to stocks US 31 4s of 1978 1983 declined from 1033 8, or 307%, in early 1958, to 827 8, or 442%, in late 1959 The average of corporate bond prices declined about 18%, to yield 457% This decline lasted one year and five months It penetrated deeply down toward the historic lows of the market since specie resumption in 1879 Only in the crisis years around 1920 and 1932 had yields of prime corporate and government bonds averaged much higher If allowance is made for the value of tax exemption, prime municipal yields had never been higher In 1959 the rediscount rate rose to 4%, its high since 1930; commercial paper rates rose to 4.

group is the most frequently used N-protecting group since it can be hydrolyzed, usually with 25 50% tri uoroacetic acid (TFA) in methylene chloride, without affecting the polymer support polypeptide bond (i.e., the benzyl ester bond formed in the rst step in Fig. 9-3).

After attachment of the rst amino acid to the polymer support, the amino group must be deprotected (i.e., the Boc group removed) to allow a second amino acid residue to be added. The resulting ammonium salt is neutralized with a tertiary amine such as N,N-diisopropylethylamine, and the free amino group of the bound amino acid is ready for coupling with a second amino acid. The second amino acid is also used in the form of the N-protected derivative. The reaction between the carboxyl group of the second amino acid and the amino group of the rst amino acid residue is carried out under conditions that increase the reactivity of the carboxyl group since this reactivity is rather low at the ambient or moderate temperatures employed in solid-phase synthesis. A variety of more active derivatives of the carboxyl group (e.g., acid chloride, anhydride, ester) are possible. Dicyclohexylcarbodiimide (DCC) is commonly used as an activator for the condensation reaction since it results in high reaction rates and yields with a general absence of side reactions. DCC is added to the N-protected amino acid and the mixture reacted with the polymer substrate without isolation of the intermediate. The active intermediate is the O-acyl isourea (XXXXVI), formed by reaction with the carboxyl group, which undergoes nucleophilic attack by the amino group of an amino acid.

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