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Peptide coupling of unprotected amino acids through in situ p-nitrophenyl ester formation

✍ Scribed by Paul Gagnon; Xicai Huang; Eric Therrien; Jeffrey W. Keillor

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
80 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Several series of dipeptides and tripeptides were prepared via an activation-coupling method involving the in situ formation of a p-nitrophenyl ester of an (N-protected) amino acid, followed by coupling with an unprotected amino acid in partially aqueous solutions. The resulting peptide is easily isolated by precipitation. In general, the yields obtained are good to excellent and racemization is minimal. This method is particularly advantageous with respect to its simplicity and lack of obligatory side chain protection/deprotection steps.

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A highly efficient one-pot deprotection/peptide coupling protocol of N-Alloc amino acids with activated N-Boc or N-Fmoc amino acids was developed in solution and on solid phase. DABCO was found to be especially effective for the deprotection of the N-Alloc group, resulting in short reaction times (1