A new ligation method for N-terminal tryptophan-containing peptides using the Pictet–Spengler reaction

doi:10.1016/S0040-4039(00)00592-X

Tetrahedron Letters

Volume 41, Issue 21, 29 May 2000, Pages 4069-4073

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Abstract

Application of a carbon–carbon bond forming reaction for ligating unprotected peptides in acetic acid is described based on a Pictet–Spengler condensation. The peptide segments include a peptide with a Trp at the N-terminal and another with a C-terminal aldehyde, which can be generated through a new cyclic acetal resin.

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Acknowledgements

This work was supported in part by U.S. Public Health Service NIH Grants GM57145, CA36544 and AI46164. We would like to thank Dr. John Mayer, Dr. Bob Anderson, Dr. Wayne Kohn and the Sphinx combinatorial chemistry group at Cambridge for helpful discussions.

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