163810-26-2Relevant articles and documents
Structural Revision of Baulamycin A and Structure-Activity Relationships of Baulamycin A Derivatives
Sengupta, Sandip,Bae, Munhyung,Oh, Dong-Chan,Dash, Uttam,Kim, Hak Joong,Song, Woon Young,Shin, Injae,Sim, Taebo
, p. 12947 - 12966 (2017)
Total synthesis of the proposed structure of baulamycin A was performed. The spectral properties of the synthetic compound differ from those reported for the natural product. On the basis of comprehensive NMR study, we proposed two other possible structur
Design and synthesis of the stabilized analogs of belactosin A with the unnatural cis-cyclopropane structure
Kawamura, Shuhei,Unno, Yuka,Asai, Akira,Arisawa, Mitsuhiro,Shuto, Satoshi
supporting information, p. 6615 - 6622 (2013/09/24)
The belactosin A analog 2a, having the unnatural cis-cyclopropane structure instead of the trans-cyclopropane structure in belactosin A, is a much more potent proteasome inhibitor than belactosin A. However, its cell growth inhibitory effect is rather lower than that expected from its remarkable proteasome inhibitory effect, probably due to its instability under cellular conditions. We hypothesized that the instability of 2a was due to chemical and enzymatic hydrolysis of the strained β-lactone moiety. Thus, to increase the stability of 2a by chemical modification, its analogs with a sterically more hindered β-lactone moiety and/or cyclopropylic strain-based conformational restriction were designed and synthesized, resulting in the identification of a stabilized analog 6a as a proteasome inhibitor with cell growth inhibitory effects. Our findings suggest that the chemical and biological stability of 2a is significantly affected by the steric hindrance around its β-lactone carbonyl moiety and the conformational flexibility of the molecule.
Fluoroalkenes as peptide isosteres: Ground state analog inhibitors of thermolysin
Bartlett,Otake
, p. 3107 - 3111 (2007/10/02)
Tripeptide analogs of the form Cbz-GlyΨ[(Z/-CF=CH]LeuXaa (1, Xaa = Gly, Ala, Leu, Phe, and NH2) were synthesized to assess the ability of the fluoroalkene moiety to mimic a peptide linkage. These compounds are modest inhibitors of the zinc endo