692778-52-2Relevant academic research and scientific papers
Three-dimensional structure-activity relationship study of belactosin A and its stereo- and regioisomers: Development of potent proteasome inhibitors by a stereochemical diversity-oriented strategy
Yoshida, Keisuke,Yamaguchi, Kazuya,Mizuno, Akira,Unno, Yuka,Asai, Akira,Sone, Takayuki,Yokosawa, Hideyoshi,Matsuda, Akira,Arisawa, Mitsuhiro,Shuto, Satoshi
experimental part, p. 1868 - 1877 (2009/06/28)
The development of potent proteasome inhibitors based on the stereochemical diversity-oriented strategy using a conformationally rigid cyclopropane structure was investigated. Thus, a series of stereo- and regioisomeric analogs of belactosin A (2), a cycl
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.
Total synthesis of (+)-belactosin A.
Armstrong, Alan,Scutt, James N
, p. 510 - 511 (2007/10/03)
A concise first total synthesis of the antitumour antibiotic belactosin A is reported, involving coupling of beta-lactone carboxylic acid 3 with N-Ala-aminocyclopropyl alanine 11.
