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Enzymatic syntheses of N-protected Leu-enkephalin and some oligopeptides in organic solvents

✍ Scribed by Yun-Hua Ye; Gui-Ling Tian; Guo-Wen Xing; Dong-Cheng Dai; Gang Chen; Chong-Xi Li

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 679 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00737-6

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✦ Synopsis

Enzymatic syntheses ofbioacitive pentapeptide, N-protected Leu-enkephalin and some other oligopeptides in organic solvents were studied. The stereoselectivity of the enzymatic reaction was examined by using racemic substrates. Different enzymes, solvent systems and protecting groups were compared. The importance of the essential water was addressed. The side chain of tyrosine was not protected during all the enzymatic reactions. P-DL-AIaOY (P=Z or Boc, Y=H or Me) and P-DL-TyrOEt were coupled with GIyNHNHPh by papain and ct-chymotrypsin in mixed solvent or organic solvent to obtain the expected optically pure products P-L-AIaGlyNHNHPh and P-L-TyrGIyNHNHPh respectively in good yield. Two sweetener precursors, ZAspXaaOR (XaaOR=PheOMe or AlaOcHex) were synthesized by thermolysin in tert-amyl alcohol and some reaction conditions were optimized to get the best yield. Full enzymatic synthesis of N-protected Leu-enkephalin ZTyrGlyGlyPheLeuOH was investigated using ct-chymotrypsin and thermolysin as catalysts in dichloromethane and tert-amyl alcohol.

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