P P CH2NH2 + HOOCCH2 CH2OOC CH2NH OCCH2 CH2OOC PAM linker CHR CHR NH Boc in .NET

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P P CH2NH2 + HOOCCH2 CH2OOC CH2NH OCCH2 CH2OOC PAM linker CHR CHR NH Boc
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The PAM linker increases the acid stability of the anchored rst amino acid residue by a factor of more than 100 compared to the simple benzyl ester. This approach uses an aminomethylated polystyrene support (usually referred to as PAM resin) instead of the chloromethylated polystyrene. Most solid-phase syntheses of polypeptides are now performed using the PAM resin. Protecting groups for the side chain COOH or NH2 groups are chosen for high stability under conditions used for hydrolysis of Boc end groups. For example, p-toluenesulphonyl (arginine, histidine), 2-chlorobenzyloxycarbonyl (lysine), 2,4-dinitrophenyl (histidine), cyclohexyl ester (aspartic and glutamic acids), 2-bromobenzyloxycarbonyl (tyrosine), N-formyl (tryptophan), and 4-methylbenzyl (cysteine) are used. These protecting groups are quite stable to the conditions (25 50% anhydrous TFA) used for hydrolysis of Boc groups. Side reactions encountered during deprotection of the side groups and cleavage of the polypeptide from the polymer support are minimized by using a two-step hydrolytic sequence, referred to as the low high HF procedure. The initial step involves 25% HF, 65% dimethylsul de, and 5% each of p-cresol and p-thiocresol, conditions that foster SN2 reaction over SN1 and thus avoids undesirable acylation and alkylation side reactions. The subsequent hydrolytic step employs 90% HF and 5% each of p-cresol and p-thiocresol to remove the more resistant protecting groups ( p-toluenesulphonyl, 4-methylbenzyl, and cyclohexyl ester).
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REACTIONS OF POLYMERS
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An alternate strategy has developed to deprotect the amino group of each amino acid residue without affecting the side group protecting groups and the polymer support polypeptide bond. This strategy involves the use of the 9- uorenylmethoxycarbonyl (Fmoc) protecting group instead of the Boc group. The key to this strategy is that the Fmoc group can be cleaved with base instead of acid (piperidine in DMF or methylene chloride). The protecting groups used for amino acid side groups are mostly ether, ester, and urethane derivatives based on t-butyl alcohol. The side-group protecting groups and the polymer support polypeptide bond, which are stable toward base, are subsequently cleaved by TFA instead of HF. The strategy based on the Fmoc protecting group is second only to that based on the Boc group for solid-phase synthesis of polypeptides. Another limitation to the solid phase of polypeptides is that the maximum yield of coupling and deprotection reactions is 99.5 99.8% instead of 100%. This has been ascribed to the less than complete compatibility of the polymer support with the reagents and/or growing polypeptide chain, although not all workers accept this explanation [Kent, 1988]. Efforts to overcome this problem have included the introduction of spacer groups on the benzene ring, for example, CH2 CH2 CH2 instead of CH2 . This results in greater compatibility and exibility of the reaction site for attachment of the rst amino acid residue and of the growing polypeptide chain. Another solution, the use of polymers more polar than polystyrene, for example, poly[dimethylacrylamide], is being explored. This also includes soluble polymer supports such as PEG. However, polystyrene remains the polymer support of choice.
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The success of solid-phase synthesis of polypeptides has stimulated efforts to use polymer substrates in other biochemical and organic syntheses: 1. The solid-phase approach has been extended to the synthesis of nucleic acids (polynucleotides) and oligosaccharides [Frechet, 1980a,b; Gait, 1980; Itakura et al., 1984; Narang, 1983; Seeberger, 2001]. The interest in synthesizing nucleic acids is usually coupled with recombinant DNA technology to synthesize polypeptides (both naturally occurring polypeptides and their analogs). The very large effort in this area at present makes this one of the most important applications of the polymer substrate method. 2. Conversion of one functional group in a molecule containing two (or more) functional groups can be achieved by covalently bonding the molecule to a polymer support through one (or more) of the functional groups. The latter group(s) is(are) protected while reactions are carried out on the unprotected group [Blossey and Ford, 1989; Hodge, 1988]. An example is the selective acylation of XXXXVII at the hydroxyl group on C-3 [Frechet, 1980a,b]. Treatment of XXXXVII with poly( p-styryl boronic acid) protects the hydroxyls at C-2 and C-4 and allows acylation at C-3. The polymer support is hydrolytically cleaved from the product with regeneration of the original protecting group. The same approach has been described for the monoderivitization of diacids, dialdehydes, diamines, and other difunctional compounds [Leznoff, 1978]. 3. Undesirable intermolecular reactions can be avoided during certain synthetic conversions. Thus it is often useful to carry out C-alkylation and C-acylation of compounds that form enolate anions, for example, esters with a-hydrogens. Such reactions are often complicated by self-condensation since the enolate anion can attack the carbonyl group of a second ester molecule. Attachment of the enolizable ester to a polymer support at low loading levels allows the alkylation and acylation reactions (Eq. 9-79) to be performed under
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