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Solid phase synthesis of cyclic peptides: model studies involving i−(i+4) side chain-to-side chain cyclisation

✍ Scribed by Vittoria Cavallaro; Philip Thompson; Milton Hearn

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 131 KB
Volume: 4
Category: Article
ISSN: 1075-2617
DOI: 10.1002/(sici)1099-1387(199808)4:5<335::aid-psc155>3.0.co;2-#

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✦ Synopsis

Conditions for the synthesis of i -(i +4) side chain-to-side chain head-to-tail Lys Glu and Glu Lys linked cyclic peptides related to hypoglycaemic analogues of human growth hormone hGH [6-13] have been examined. The success of the cyclisation reaction with the corresponding resin-bound, partially protected linear peptides was found to be both reagent as well as sequence dependent, with competing inter-chain oligomerisation predominating in some cases. The results also indicated that protection with the bulky Fmoc group of the amino acid residues immediately adjacent to the side chain-deprotected Lys and Glu residues, which participate in the cyclisation reaction, enhanced the rate of lactam formation.

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