115114-87-9Relevant articles and documents
An efficient synthesis of enantiomerically pure (R)-(2-benzyloxyethyl)oxirane from (S)-aspartic acid
Frick,Klassen,Bathe,Abramson,Rapoport
, p. 621 - 623 (1992)
A 3-step synthesis of the title compound from (S)-aspartic acid is described. The overall yield of this process is 65% and the enantiomeric purity (ep) of the product is greater than 99%.
Studies toward the stereoselective synthesis of C13 to C21 fragment of the brasilinolides family of immunosuppressive macrolides
Ravindranath, Hajari,Sharma, Gangavaram V. M.
, p. 2485 - 2490 (2015)
The work describes our attempts to synthesize the C13 to C21 fragment of brasilinolides, a 32-membered macrolide class of molecule. The C13 to C21 segment encompasses six asymmetric centers and a pyran ketal moiety. The synthesis starts from L-malic acid,
Stereoselective total synthesis of C2-symmetric natural products pyrenophorol and its derivatives
Narala, Siva Ganesh,Nagalatha,Venkat Narsaiah
supporting information, p. 2173 - 2178 (2019/03/11)
A stereoselective total synthesis of 16-membered C2-symmetric macrodiolide Pyrenophorol, Tetrahydropyrenophorol and 4,4-diacetylpyrenophorol have been accomplished. The synthesis started from commercially available L-Aspartic acid and the key reactions involved are regioselective epoxide opening, CBS reduction, Pinnick oxidation and Mitsunobu dilactonization.
Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents
Choi, Hyunsuk,Ham, So-Young,Cha, Eunji,Shin, Yujin,Kim, Han-Shin,Bang, Jeong Kyu,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo
supporting information, p. 9821 - 9837 (2017/12/26)
Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.
