69632-44-6Relevant academic research and scientific papers
Chiral separation on various modified amino alcohol-derived HPLC chiral stationary phases
Yu, Jeongjae,Lee, Jung Mi,Ryoo, Jae Jeong
, p. 276 - 281 (2016/03/19)
3,5-Dinitrobenzoyl chloride was previously used for the preparation of (R)-phenylglycinol- and (S)-leucinol-derived chiral stationary phases. In this study, 3,5-bis(trifluoromethyl)benzoyl chloride, 2-furoyl chloride, 2-theonyl chloride, 10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride, diphenylcarbamoyl chloride, and 1-adamantanecarbonyl chloride were used to prepare six new phenylglycinol-derived chiral stationary phases (CSPs) and five new leucinol-derived CSPs. Using these 11 CSPs, chiral separation of nine π-acidic amino acid derivatives and five π-basic compounds was performed, and the separation results were compared. An adamantyl-derived CSP showed good separation.
Preparation of two new diasteromeric chiral stationary phases based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid and (R)- or (S)-1-(1-naphthyl)ethylamine and chiral tethering group effect on the chiral recognition
Agneeswari, Rajalingam,Sung, Ji Yeong,Jo, Eun Sol,Jeon, Hee Young,Tamilavan, Vellaiappillai,Hyun, Myung Ho
, (2016/08/30)
Two new diastereomeric chiral stationary phases (CSPs) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral tethering group and a Π-basic chiral unit such as (R)-1-(1-naphthyl) ethylamine (CSP 1) or (S)-1-(1-naphthyl)ethylamine (CSP 2) were prepared. The two CSPs were applied to the enantiomeric separation of N-(3,5-dinitrobenzoyl)-1-phenylalkylamines and N-(3,5-dinitrobenzoyl)-α-amino acid derivatives using 20% isopropyl alcohol in hexane as a normal mobile phase. To elucidate the effect of the two chiral units on the chiral recognition, the chiral recognition abilities of the two CSPs were compared with each other and with that of a CSP (CSP 3) based on (R)-1-(1-naphthyl)ethylamine. From the chromatographic chiral recognition results, (R)-1-(1-naphthyl)ethylamine and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 1 were concluded to show a cooperative ("matched") effect on the chiral recognition while (S)-1-(1-naphthyl)ethylamine and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 2 were concluded to show an uncooperative ("mismatched") effect on the chiral recognition. From these results, it was concluded that (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid can be successfully used as a chiral tethering group for the preparation of new CSPs.
Design, synthesis and SAR studies of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine as aminopeptidase N/CD13 inhibitors
Shang, Luqing,Fang, Hao,Zhu, Huawei,Wang, Xuejian,Wang, Qiang,Mu, Jiajia,Wang, Binghe,Kishioka, Shiroh,Xu, Wenfang
experimental part, p. 2775 - 2784 (2009/08/15)
Aminopeptidase N (APN), belonged to metalloproteinase, is an essential peptidase involved in the process of tumor invasion and metastasis. A series of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine were designed, synthesized and evaluate
Enantioselective hydrolysis of N-acylated α-amino esters at a biphasic interface: Tandem reaction kinetic resolution using a chiral complexing agent
Snyder, Seth E.,Pirkle, William H.
, p. 3283 - 3286 (2007/10/03)
equation presented Highly enantioselective hydrolytic kinetic resolutions of esters derived from N-acylated α-amino acids proceed rapidly at hydrocarbon/water interfaces in the presence of a proline-derived chiral selector. When performed in tandem with an enantioselective biphasic esterification reaction, esters of 100% enantiomeric excess are obtained.
