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Synthesis of the Isotopically LabelledC-Terminal Fragment of Zervamicin: An Approach to the Synthesis of Aib-Containing Peptides

✍ Scribed by Ogrel, Alexei ;Bloemhoff, Wim ;Lugtenburg, Johan ;Raap, Jan

Book ID
102901196
Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
768 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The isotopically labelled C‐terminal fragment of zervamicin, H‐Hyp^10^‐[4,4‐^2^H~2~‐Gln]‐Aib‐Hyp‐Aib‐Pro‐Phl^16^, has been synthesized in solution by a Fmoc/tert‐butyl strategy in 28% overall yield. The Fmoc group was removed by reaction for 2 min with 0.1 M NaOH in dioxane/methanol/water, (30:9:1, v:v:v). The couplings of the sterically hindered Aib residues were achieved by means of either BOP/DMAP activation or Fmoc‐Aib‐Cl. Acid deprotection of the peptide was performed by reaction with 50% TFA in CH~2~Cl~2~ for 30 min without significant cleavage of the acid‐labile Aib‐Pro and Aib‐Hyp peptide bonds.

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