Racemization in Peptide Synthesis

作者: D.S. KEMP

DOI: 10.1016/B978-0-12-304201-9.50013-8

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摘要: Publisher Summary This chapter discusses the racemization in peptide synthesis. Epimerization at amino acid α-carbon has plagued field of polypeptide synthesis throughout its history, placing severe constraints on development satisfactory synthetic routes to these molecules. Percentages or rates exchange hydrogen isotopes an aminoacyl derivative can be equated with percentages provided it shown that loss chirality this site occurs same rate as exchange. It is found if α-hydrogen not isotopically homogeneous, kinetic isotope effects enolization are expected and lead misleading discrimination. Several derivatives have been demonstrated exhibit phenomenon isoracemization, exceeding those for by much twentyfold. Racemization acids under strongly acidic aqueous conditions particularly pertinent behavior used protein hydrolysis, prior analysis. basic long noted a relatively rapid process, bear electron-withdrawing α-conjugating substituents.

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