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Huang, Haofei,Nandhakumar, Raju,Choi, Misun,Su, Zhishan,Kim, Kwan Mook American Chemical Society 2013 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.135 No.7
<P>The chiral ketone (<I>S</I>)-<B>3</B> shows high kinetic enantioselectivities toward the <SMALL>l</SMALL> form for general underivatized amino acids with hydrophobic side chains and a high thermodynamic enantioselectivity toward the <SMALL>d</SMALL> form for cysteine with its −SH polar side chain when used as an extractant in enantioselective liquid–liquid extractions in the presence of Aliquat 336. Consecutive extractions by imine formation and hydrolysis increase the enantiopurity of the amino acid, as both of these reactions are <SMALL>l</SMALL>-form-selective.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2013/jacsat.2013.135.issue-7/ja3105945/production/images/medium/ja-2012-105945_0011.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja3105945'>ACS Electronic Supporting Info</A></P>
Qian Chen,Ying-Ji Jin,Haofei Huang,Zhishan Su,김성규,김관묵 대한화학회 2018 Bulletin of the Korean Chemical Society Vol.39 No.8
The derivative of aminophenyl-aldehyde with an asymmetric carbon and an uryl group, (S)-2, was synthesized. The combination of (S)-2 and aliquat-336 in CDCl3 extracted underivatized amino acids in water layer by imine formation with enantioselectivities of 12/1 for Phe, 13/1 for Val, and 12/1 for Leu, which are comparable with those of previously reported binaphthol-based extractor (S)-1. The enantioselectivities of (S)-2 is remarkable considering the low molecular weight compared to (S)-1. Density functional theory computations and experimental data demonstrate that imine bond is strengthened by resonance-assisted hydrogen bond with the nearby ?NH? group.
Ying-Ji Jin,Yun Seo Choi,Qian Chen,Mukesh Eknath Shirbhate,Haofei Huang,김영미,김성진,전무진,Eon Cheol Koo,김관묵 대한화학회 2016 Bulletin of the Korean Chemical Society Vol.37 No.10
Axially chiral binaphthoic acid (BNA) was studied as a resolving agent for a stereoselective crystallization of 1-(4-chlorophenyl)ethylamine (CPEA). The diastereomeric pair of (R)-BNA/(S)-CPEA crystallizes in methylene chloride, on the other hand, the pair of (S)-BNA/(S)-CPEA crystallizes in acetone. The switch of the solubility of the diastereomeric pair is due to the imine formation with acetone. The very low solubility of the BNA/imine pair appears to be responsible for the fast and complete imine formation. The crystal structure of the BNA part in both crystals of the diastereomers maintains a same feature. Asymmetric chiral channels and pockets composed by intermolecular packing of BNA molecules appear in the crystal structures, and the robustness of them seem to contribute to the recognition of the chirality of CPEA with high selectivity.
Zhaoyi Li,Liang Sun,Zhongjun Fu,Yuchao Li,Zhaohui Jiang,Bingtao Tang,Quan Ji,Yanzhi Xia,Ming Wang,Haofei Huang 한국섬유공학회 2021 Fibers and polymers Vol.22 No.3
Calcium alginate fiber is a biomaterial with promising application in textile industry. However, the poor dyeingproperty of this fiber restricts its development. In this study, three PVAm (polyvinylamine) dyes were applied to the exhaustdyeing of calcium alginate fiber and their dyeing behavior under different dyeing conditions was studied. The dyeing resultsrevealed that PVAm dyes were firmly adsorbed on calcium alginate fiber by coordination bonding formed between theprimary amino groups in PVAm backbones of dyes and Ca2+ ions in calcium alginate fiber. This special complex dyeingmode was further confirmed by a Langmuir-type adsorption manner of PVAm-1 dye for calcium alginate fiber. By theformation of this stable chelation structure between dyes and fibers, high exhaustion rates (88.9-97.1 %) and excellent colorfastness were obtained. SEM and XRD results also showed that the surface and crystal phase of dyed fibers had very slightchanges compared to those of original calcium alginate fibers. The strength property of the fiber was also maintained wellafter this special complex dyeing process.