Summary
We have found that guanidine acetate catalyses the transformation of a β-benzyl-aspartyl peptide (Boc-Asp-(OBzl)-Leu-Trp-OMe) to an aminosuccinyl peptide (Boc-Asu-Leu-Trp-OMe). The reaction was accompanied by partial epimerization. However, not even a small amount of epimerization could be detected when the aminosuccinyl peptide was synthesised from Boc-Asp-Leu-Trp-OMe with the addition of DIC, HOPfp and guanidine acetate (as a catalyst). This reaction seems to be suitable for the epimerization-free solid phase synthesis of aminosuccinyl peptides, e.g. Asu6-Lamprey-III-GnRH (Glp-His-Trp-Ser-His-Asu-Trp-Lys-Pro-Gly-NH2).
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Vadasz, Z., Seprodi, J. & Teplan, I. Studies on epimerization-free methods for the preparation of aminosuccinyl peptides. Lett Pept Sci 2, 339–344 (1996). https://doi.org/10.1007/BF00119997
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DOI: https://doi.org/10.1007/BF00119997