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Total Enzymatic Synthesis of the Cholecystokinin Octapeptide (CCK-8)

✍ Scribed by Rajendra Joshi; Liping Meng; Heiner Eckstein

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
183 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The enzymatic synthesis of the cholecystokinin octapeptide (CCK‐8) is reported. The target octapeptide CCK‐8 is the minimum active sequence with the same biological activity as naturally occurring cholecystokinin and is a potential therapeutic agent in the control of gastrointestinal function as well as a drug candidate for the treatment of epilepsy and obesity. The protected CCK‐8 was obtained by incubation of Bz‐Arg‐Asp(OEt)‐Tyr‐Met‐OAl and Gly‐Trp‐Met‐Asp(OMe)‐Phe‐NH~2~ with immobilized α‐chymotrypsin. The Bz‐Arg group was used as an N‐terminal protecting group in the synthesis of the tripeptide fragment. The protected CCK‐8 was treated with trypsin to remove the Bz‐Arg group successfully. Free or immobilized enzymes were used as catalysts. The effect of the acyl donor ester structure, the C(α) protecting group of the nucleophile, reaction media, enzyme, and the carrier of the enzymes on the outcome of the coupling reaction was studied.

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The enzymatic synthesis of the tripeptide derivative Z-Gly-Trp-Met-OEt is reported. This tripeptide is a fragment of the cholecystokinin C-terminal octapeptide CCK-8. Studies on the a-chymotrypsin catalyzed coupling reaction between Z-Gly-Trp-R, and Met-R, have focused on low water content media, us