Options for Preparing Peptide Amides

FIGURE 8.6 Synthesis of /V-protccted dipeptide amides (A) and methylamides (B) by ami-nolysis of the unisolated succinimido ester obtained through the mixed anhydride in CH2C12.22 The products contained 0.5% of epimerized compound. HONSu = /V-hydroxysuccinimde, NMM = Af-methylmorpholine. 

Benzhydryl- (phenylbenzyl) and 4-methylbenzhydrylamine resins (see Section 5.18) are available for preparing primary amides, using Boc/Bzl chemistry. 4-Methylben-zhydrylamine, Rink amide, Sieber amide and dhnethoxytritylamine resins and the linkers PAL and XAL (see Section 5.20) are available for preparing primary amides, using Fmoc/tBu chemistry. Secondary amides can be synthesized by making use of AJ-alkyl-Sieber or ALalkyl-PAL linkers. 

JT Lobl, L Maggiore. Convenient synthesis of C-terminal peptide analogues by aminolysis of oxime resin-linked protected peptides. J Org Chem 53, 1979, 1988. 

JC Hendrix, JT Jarrett, ST Anisfield, PT Lansbury. Studies related to a convergent fragment-coupling approach to peptide synthesis using the Kaiser oxime resin. J Org Chem 57, 3414, 1992. 

N Voyer, A Lavoie, M Pinette, J Bernier. A convenient solid phase preparation of peptide subtituted amides, (oxime resin) Tetrahedron Lett 35, 355, 1994. 

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