In:
European Journal of Organic Chemistry, Wiley, Vol. 2008, No. 15 ( 2008-05), p. 2592-2600
Abstract:
A backbone amide linker strategy was chosen for the solid‐phase synthesis of triazole‐containing cyclic tetra‐ and pentapeptides. An alkyne‐substituted linker derived from 4‐hydroxy‐2‐methoxybenzaldehyde was elongated by using standard “Fmoc‐based” solid phase chemistry and terminated by coupling of an azido acid. In solution, the peptides were cyclized by a Cu I ‐catalyzed azide‐alkyne cycloaddition reaction. The solid‐supported synthesized linear peptides had to be cleaved prior to cyclization. As an example of cyclic tetrapeptides, a triazole analog of cyclo ‐[Pro‐Val‐Pro‐Tyr] ( 2 ) was prepared by the solid‐phase/solution‐phase method. For the cyclic pentapeptides, segetalin B ( 3 ) was chosen as a model compound to show the applicability of this method.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2008:15
DOI:
10.1002/ejoc.200800143
Language:
English
Publisher:
Wiley
Publication Date:
2008
detail.hit.zdb_id:
1475010-7
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