Stereochemical control in the preparation of α-amino N-methylthiazolidine masked aldehydes used for peptide aldehydes synthesis

Chiral N-methyl thiazolidines masked α-amino aldehydes are used for solid phase peptide aldehyde elongation. Contrary to N-Boc-protected α-amino aldehydes, N-trityl protection secures the chiral integrity of the incoming aldehyde chiral C1′ carbon atom during condensation of the amino aldehydes with...

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Bibliographic Details
Published in:Tetrahedron 2002-03, Vol.58 (13), p.2673-2680
Main Authors: Gros, Christel, Boulègue, Cyril, Galeotti, Nathalie, Niel, Gilles, Jouin, Patrick
Format: Article
Language:English
Subjects:
ligation
N-trityl
peptide aldehyde
solid phase
thiazolidine
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Summary:Chiral N-methyl thiazolidines masked α-amino aldehydes are used for solid phase peptide aldehyde elongation. Contrary to N-Boc-protected α-amino aldehydes, N-trityl protection secures the chiral integrity of the incoming aldehyde chiral C1′ carbon atom during condensation of the amino aldehydes with l-cysteinyl residues. The Ac-Tyr-Val-Ala-Asp-H caspase inhibitor was prepared on a solid support starting from the N-trityl-amino thiazolidine masked aspartinal as a validation of this process. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00115-1