1046470-58-9Relevant academic research and scientific papers
Synthesis of 2,3- and 3,4-methanoamino acid equivalents with stereochemical diversity and their conversion into the tripeptide proteasome inhibitor belactosin a and its highly potent cis-cyclopropane stereoisomer
Yoshida, Keisuke,Yamaguchi, Kazuya,Sone, Takayuki,Unno, Yuka,Asai, Akira,Yokosawa, Hideyoshi,Matsuda, Akira,Arisawa, Mitsuhiro,Shuto, Satoshi
supporting information; experimental part, p. 3571 - 3574 (2009/05/07)
(Chemical Equation Presented) A series of chiral 2,3- and 3,4-methanoamino acid equivalents of stereochemical diversity were designed and synthesized from our chiral cyclopropane units, using a diastereoselective Grignard addition with (R)- or (S)-t-butanesulfinyl imines as the key step. These equivalents were converted into the proteasome inhibitor belactosin A and its cis-cyclopropane stereoisomer. The unnatural cis-isomer was shown to be more than twice as potent as belactosin A as a proteasome inhibitor.
