Abstract
Treatment of a mixture of Cys(R)(O) and Cys(R′) with an acid was found to generate cystine in fairly good yields, when suitable R, R′, and an acid were selected. An unsymmetrical cystine peptide was prepared by treatment of a mixture of Z(OMe)-Cys(R) (0)-Ala-NH2 (R=Acm or MBzl) and Z(OMe)-Cys(MBzl)-Gly-OBzl with TFA or 1 M TFMSA/TFA.3 Oxytocin was obtained in an excellent yield by TFA treatment of the protected peptide containing Cys(Acm)(0) and Cys(MBzl). Thus, formation of the disulfide bond was found feasible at the position of Cys(R) (0).
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Abbreviations
- Boc:
-
t-butyloxycarbonyl
- Z(OMe):
-
p-methoxybenzyloxycarbonyl
- MBzl:
-
p-methoxybenzyl
- Acm:
-
acetamidomethyl
- Bzl:
-
benzyl
- Ad:
-
l-adamantyl
- tBu:
-
t-butyl
- TFA:
-
trifluoroacetic acid
- TFMSA:
-
trifluoromethanesulfonic acid
- TMSOTf:
-
trimethylsilyl trifluoromethane sulfonate
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Fujii, N., Otaka, A., Funakoshi, S. et al. Studies on peptides CLVIII. Model experiments for the synthesis of open-chain unsymmetrical cystine-peptides. J Protein Chem 7, 151–156 (1988). https://doi.org/10.1007/BF01025244
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DOI: https://doi.org/10.1007/BF01025244