Journal of the Chemical Society. Perkin transactions I p. 175 - 182 (1996)
Update date:2022-08-02
Topics:
Offer, John
Quibell, Martin
Johnson, Tony
The N-(2-acetoxy-4-methoxybenzyl) (AcHmb) backbone amide-protecting group has been applied in an on-resin solid-phase synthesis of asparagine N-linked glycopeptides. Backbone protection of the -Asp(OAllyl)-Ala- aspartyl amide bond suppressed the formation of aspartimide during both the initial chain assembly and the subsequent activation and glycosylation of the aspartyl β-carboxy group. A 1.1-1.25 mole excess of glycosylamine coupled quantitatively, with minimal side reaction, to the activated aspartyl β-carboxy group of the fully assembled backbone-protected peptide-resin. A parallel synthesis without backbone amide protection produced substantial aspartimide peptide, particularly during the initial chain assembly.
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Doi:10.1016/0022-328X(95)05865-M
(1996)Doi:10.1016/0040-4039(95)02278-3
(1996)Doi:10.1016/S0040-4039(00)71644-3
(1967)Doi:10.1021/jm950918e
(1996)Doi:10.1016/0040-4039(96)00117-7
(1996)Doi:10.1016/0040-4020(96)00085-3
(1996)
