Carbopeptides: Chemoselective ligation of peptide aldehydes to an aminooxy-functionalized D-galactose template
Carbopeptides: Chemoselective ligation of peptide aldehydes to an aminooxy-functionalized D-galactose template
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DOI：
10.1002/1099-1387(200006)6:6
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发表时间：
2000-06-01
影响因子：
2.1
通讯作者：
Jensen, KJ
中科院分区：
文献类型：
--
作者：
Brask, J;Jensen, KJ
Multifunctional, topological template molecules such as linear and cyclic peptides have been used for the attachment of peptide strands to form novel protein models of, for example, 4-alpha-helix bundles, The concept of carbohydrates as templates for de novo design of potential protein models has been previously described and these novel chimeric compounds were termed carbopeptides, Here, a second generation strategy in which carbopeptides are synthesized by chemoselective ligation of a peptide aldehyde to an aminoxy-functionalized alpha-D-galactopyranoside is described. This template was prepared by per-O-acylation of methyl alpha-D-galactopyranoside with N,N-Boc(2)-aminooxyacetic acid to form a tetra-functionalized template, followed by treatment with TFA-CH2Cl2 to release the aminooxy functionality. The peptide aldehydes Fmoc-Ser-Gly-Gly-H and H-Ala-Leu-Ala-Lys-Leu-Gly-Gly-H were synthesized by a BAL strategy. Four identical copies of peptide aldehyde were smoothly attached to the template by chemoselective ligation to form a 2.1 and a 2.9 kDa carbopeptide, respectively. Copyright (C) 2000 European Peptide Society and John Wiley & Sons, Ltd.
