Novel synthesis of various orthogonally protected C α-methyllysine analogues and biological evaluation of a Vapreotide analogue containing (S)-α-methyllysine

S Banerjee, WJ Wiggins, JL Geoghegan…

Index: Banerjee, Souvik; Wiggins, Walker J.; Geoghegan, Jessie L.; Anthony, Catherine T.; Woltering, Eugene A.; Masterson, Douglas S. Organic and Biomolecular Chemistry, 2013 , vol. 11, # 37 p. 6307 - 6319

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Citation Number: 10

Abstract

Prochiral malonic diesters containing a quaternary carbon center have been successfully transformed into a diverse set of tBoc-Fmoc-α2, 2-methyllysine-OH analogues through chiral malonic half-ester intermediates obtained via enzymatic (Pig Liver Esterase, PLE) hydrolysis. The variety of chiral half-ester intermediates, which vary from 1 to 6 methylene units in the side chain, are achieved in moderate to high optical purity and in good yields. ...