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Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist

✍ Scribed by Nicolette C. Ross; Santosh S. Kulkarni; Jay P. McLaughlin; Jane V. Aldrich

Book ID
104098107
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
311 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

The tryptophan isomers of the cyclic tetrapeptide CJ-15,208, reported to be a kappa opioid receptor (KOR) antagonist [Saito, T.; Hirai, H.; Kim, Y. J.; Kojima, Y.; Matsunaga, Y.; Nishida, H.; Sakakibara, T.; Suga, O.; Sujaku, T.; Kojima, N. J. Antibiot. (Tokyo)2002, 55, 847-854.], were synthesized to determine the tryptophan stereochemistry in the natural product. A strategy was developed to select linear precursor peptides that favor cyclization using molecular modeling, and optimized cyclization conditions are reported. The optical rotation of the l-Trp isomer is consistent with that of the natural product. Unexpectedly both isomers exhibit similar nanomolar affinity for KOR.

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