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Preparation and application of O-amino-serine, Ams, a new building block in chemoselective ligation chemistry

✍ Scribed by Jane C. Spetzler; Thomas Hoeg-Jensen

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
131 KB
Volume
5
Category
Article
ISSN
1075-2617

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✦ Synopsis

The non-codable amino acid O-amino-serine, Ams, has been prepared in both L-and D-forms as the orthogonally protected derivative, Fmoc-Ams(Boc)-OH (1 and 2). This new amino acid derivative is useful for chemoselective ligations. Under acidic conditions and in the presence of all other common amino acid functionalities, the oxyamine function selectively forms oxime linkages with aldehydes. The Ams residue has been incorporated into both ends of the peptide sequence Asp-Leu-Trp-Gln-Lys using standard SPPS. The deprotected peptide has been used for chemical ligation to afford a peptide dimer as well as a glycopeptide. Ams racemization was found to be negligible, as monitored by HPLC separation of Ams dipeptide diastereomers.

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