A simple and efficient synthesis of an Asp-Gly dipeptide mimetic |
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Authors: | John M Ndungu |
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Institution: | Department of Chemistry, University of Arizona, Tucson, AZ 85721, USA |
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Abstract: | Alkylation of Nα-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral β-allyl substituted aspartic acid in good yields. After deprotection of the Nα-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with l-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics. |
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Keywords: | Bicyclic dipeptide β-substituted aspartic acid Trifluoroacetamide Cholecystokinin |
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