135722-55-3Relevant academic research and scientific papers
Synthesis of novel and conformationally constrained bridged amino acids as compact modules for drug discovery
Wu, Guolong,Kou, Buyu,Tang, Guozhi,Zhu, Wei,Shen, Hong C.,Liu, Haixia,Hu, Taishan
, p. 599 - 602 (2016)
As novel scaffolds with rigid inherent three-dimensional conformation, the bridged amino acid building blocks containing both morpholine and pyrrolidine motifs, 2-oxa-5-azabicyclo[2.2.1]heptane-4-carboxylic acid 1 and 3-oxa-8-azabicyclo[3.2.1]octane-5-carboxylic acid 2, were first synthesized as compact modules for future applications in the optimization of physicochemical and pharmacokinetic properties of drug candidates in drug discovery.
Epoxy amino acids produced from allylglycines intramolecularly cyclised to yield four stereoisomers of 4-hydroxyproline derivatives
Krishnamurthy, Suvratha,Arai, Toru,Nakanishi, Kanae,Nishino, Norikazu
, p. 2482 - 2490 (2014/01/06)
Derivatives of 2-amino-4-pentenoic acid (allylglycine) were efficiently resolved using Subtilisin or acylase. The side-chain unsaturated bond of the enantiomerically pure amino acid with tert-butoxycarbonyl (Boc) protection was smoothly epoxidized with m-chloroperbenzoic acid. When the Boc protection of the amino group was removed, the amino group intramolecularly attacked the side-chain epoxide, generating compounds with five-membered rings: the 4-hydroxyproline derivatives. Two diastereomeric products were formed through the cyclisation reaction, for example, (2S,4S)-4-hydroxyproline benzyl ester (cis-8) and (2S,4R)-4-hydroxyproline benzyl ester (trans-8) were formed from (2S)-amino acid with a side-chain epoxide. Compound (2S,4S)-4-hydroxyproline benzyl ester (cis-8) was transformed to a lactone (cis-hydroxyproline lactone, 10) with the removal of benzyl alcohol. The cis-conformation was essential for the intramolecular ester exchange reaction; in fact, no lactone formation was observed for the trans isomer (trans-8). The separation of cis-hydroxyproline lactone and the trans-isomeric hydroxyproline benzyl ester was facile and clear, in contrast to the difficult separation of cis- and trans-hydroxyproline derivatives. Thus, two diastereomers of hydroxyproline derivatives for l-hydroxyproline and also for d-hydroxyproline were obtained, i.e., four diastereomers of hydroxyproline derivatives.
Nonenzymatic enantioselective monoacetylation of prochiral 2-protectedamino-2-alkyl-1,3-propanediols utilizing a chiral sulfonamide-Zn complex catalyst
Honjo, Takashi,Nakao, Michiyasu,Sano, Shigeki,Shiro, Motoo,Yamaguchi, Kentaro,Sei, Yoshihisa,Nagao, Yoshimitsu
, p. 509 - 512 (2007/10/03)
Treatment of a chiral sulfonamide with Et2Zn gave quantitatively its Zn complex and then the structure was determined by X-ray crystallographic analysis. Reaction of prochiral W-Boc-2-amino-2-alkyl-1,3-propanediols with Ac2O in the presence of 5 mol% of chiral sulfonamide - Zn complex catalyst afforded the corresponding chiral monoacetyl products in 70-92% yields with 70-88% ee values. The proposed mechanism for the catalytic monoacetylation of a prochiral 1,3-propanediol was presented on the basis of CSI-MS analysis.
New serine protease inhibitors with leukotriene B4 (LTB4) receptor binding affinity
Nakayama, Yoshisuke,Senokuchi, Kazuhiko,Sakaki, Katsuhito,Kato, Masashi,Maruyama, Toru,Miyazaki, Toru,Ito, Hidenori,Nakai, Hisao,Kawamura, Masanori
, p. 971 - 985 (2007/10/03)
A series of new trypsin-like serine protease inhibitors, 1, 2 and 7-23, containing amidinobenzene moiety was found to show potent LTB4-receptor affinity. Among them, compounds 1 and 2 were found to be LTB4 receptor antagonists based on an inhibition assay of human polymorphonuclear neutrophil (PMN) intracellular calcium mobilization induced by LTB4. Compounds 1 and 2, which satisfy the reported structural requirements for good oral activity, are expected to show a balanced dual mode of action, i.e., protease inhibitory activity and LTB4 receptor antagonist activity, in vivo.
Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 1. Lipopeptides Containing Nonproteinogenic Amino Acids
Schneider, Helmut,Sigmund, Gerhard,Schricker, Bettina,Thirring, Klaus,Berner, Heinz
, p. 683 - 689 (2007/10/02)
Two stereoisomeric lipopeptides 1 and 2 which can be regarded as modified peptidoglycans have been synthesized by using three different reaction sequences.The ene reaction of the α-allylated dipeptide 12 with butyl glyoxylate was used as a key step.The re
