Amino acids, bromination, solid-phase

The first successful solid-phase synthesis of a peptide (H-Leu-Ala-Gly-Val-OH) was reported by Merrifield in 1963 [12]. The strategy used is outlined in Figure 16.1. The support was chloromethylated, partially nitrated (or brominated), 2% cross-linked polystyrene. Nitration was necessary to suppress acidolytic cleavage of the benzyl ester attachment during Z-group removal. Acylations of deprotected, support-bound amino acids were performed with DCC, and at the end of the synthesis the peptide was cleaved from the support by saponification with sodium hydroxide. 

Phenol-ketone novolacs 1487, 1488 Phenol-nitrile complexes 377 Phenol radical cations 1101 fragmentation of 289-291 Phenols—see also Biphenols, Bis-phenols, Hydroxybenzenes, Polyphenols acidities of, gas-phase 310-312 acylation of 629-632, 933, 934 Lewis acid catalyzed 631 montmoriUonite-catalyzed 632 pyridine-catalyzed 631 adsorption of 944 alkylation of 606-629, 941 Brdnsted acid catalyzed 612 Lewis acid catalyzed 607-611 solid acid catalyzed 612-621 stereoselective 621-626 under supercritical conditions 621 as antioxidants 139-143, 840-901 ort/io-substituted 845 thermochemistry of 139, 140, 179 autoxidation of 1118, 1119 bromination of 649-651 jr-cation interaction of 322 chlorination of 649 comparison with isoelectronic methyl, amino and fluoro aromatic derivatives 226... 

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