REVERSIBLE MODIFICATION OF THE ACID-LABILE 2-HYDROXY-4-METHOXYBENZYL (HMB) AMIDE PROTECTING GROUP - A SIMPLE SCHEME YIELDING BACKBONE SUBSTITUTED FREE PEPTIDES

Authors
QUIBELL M TURNELL WG JOHNSON T
Citation
M. Quibell et al., REVERSIBLE MODIFICATION OF THE ACID-LABILE 2-HYDROXY-4-METHOXYBENZYL (HMB) AMIDE PROTECTING GROUP - A SIMPLE SCHEME YIELDING BACKBONE SUBSTITUTED FREE PEPTIDES, Tetrahedron letters, 35(14), 1994, pp. 2237-2238
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
14
Year of publication
1994
Pages
2237 - 2238
Database
ISI
SICI code
0040-4039(1994)35:14<2237:RMOTA2>2.0.ZU;2-5
Abstract
Acetylation of the trifluoroacetic acid labile 2-hydroxy-4-methoxybenz yl (Hmb) amide protecting group (1) gave a dramatic increase in acid s tability. This enabled peptides prepared by the Fmoc/t-butyl solid pha se strategy to be deprotected and cleaved whilst retaining backbone am ide protection. Acid lability was easily restored by piperidine mediat ed de-O-acetylation.