化学
胆囊收缩素
组合化学
类阿片
立体化学
阿片肽
肽
寡肽
生物化学
受体
作者
John M. Ndungu,James P. Cain,Peg Davis,Wen Shou,Todd W. Vanderah,Josephine Lai,Frank Porreca,Victor J. Hruby
标识
DOI:10.1016/j.tetlet.2006.01.096
摘要
In our ongoing research on the synthesis of constrained analogues of CCK/opioid chimeric peptides, a bicyclic dipeptide mimetic for Nle-Asp was designed and synthesized. Starting from β-allyl substituted aspartic acids, the terminal double bond was oxidized resulting in spontaneous cyclization to form racemic hemiaminals. Allylation of the hemiaminals afforded 5-allyl substituted proline analogues, which on oxidation, Horner–Emmons olefination, asymmetric hydrogenation, and bicyclization afforded bicyclic dipeptide mimetics for Nle-Asp. Constrained CCK/opioid peptide analogues containing bicyclic dipeptide mimetics for Nle-Gly, Nle-Asp, and homoPhe-Gly were then synthesized and analyzed at both the CCK and opioid receptors.
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