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Synthesis of the Isotopically Labelled C ‐Terminal Fragment of Zervamicin: An Approach to the Synthesis of Aib‐Containing Peptides
Author(s) -
Ogrel Alexei,
Bloemhoff Wim,
Lugtenburg Johan,
Raap Jan
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970109
Subject(s) - chemistry , yield (engineering) , steric effects , peptide , methanol , cleavage (geology) , peptide synthesis , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
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.