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Use of the vinyloxycarbonyl group for amino protection in peptide synthesis

✍ Scribed by R.A. Olofson; Y.Stephen Yamamoto; David J. Wancowicz

Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
252 KB
Volume
18
Category
Article
ISSN
0040-4039

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✦ Synopsis

In this communication we introduce a promising masking agent --the vinyloxycarbonyl or VOC group --for the protection of amino functions in peptide chemistry. Amino acids are easily converted to their N-VOC derivatives (l_) in dilute aqueous base using the known vinyl chloroformate' in dioxane as the acylating agent. The pH of the reaction medium is controlled (g-10) with a pH stat or by using an MgO suspension as the OH source, two procedures' widely utilized for the preparation of BOC and Z amino acids.3 Some of the VOC amino acids made are listed in Table I.4 Like BOC-AA's, the acids (1) are often oils but are easily characterized as the crystalline dicyclohexylamnonium (DCHA) salts (2) from which j_ can be regenerated by extraction from carefully acidified solutions. Some VOC peptides (2) made Table .

Representative N-VOC Amino Acids and Peptides

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