Synthesis of Tripeptide Derivatives with Three Stereogenic Centers and Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents Derived from D-Phenylalanine and (1S,2S)-(+)-1,2-Diaminocyclohexane via 1H NMR Spectroscopy

被引:14
作者
Feng, Lei [1 ]
Gao, Guangpeng [1 ]
Zhao, Hongmei [2 ]
Zheng, Li [1 ]
Wang, Yu [1 ]
Stavropoulos, Pericles [3 ]
Ai, Lin [1 ]
Zhang, Jiaxin [1 ]
机构
[1] Beijing Normal Univ, Coll Chem, Beijing 100875, Peoples R China
[2] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100190, Peoples R China
[3] Missouri Univ Sci & Technol, Dept Chem, Rolla, MO 65409 USA
基金
中国国家自然科学基金; 美国国家卫生研究院;
关键词
THYROTROPIN-RELEASING-HORMONE; ALPHA-AMINO-ACIDS; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE RECOGNITION; NMR-SPECTROSCOPY; SHIFT-REAGENT; STEREOSELECTIVE RECOGNITION; ABSOLUTE-CONFIGURATION; HYDROXY-ACIDS; DISCRIMINATION;
D O I
10.1021/acs.joc.8b02212
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomers of a series of tripeptide derivatives with three stereogenic centers (+/-)-G1-G9 have been prepared from D- and L-alpha-amino acids as guests for chiral recognition by H-1 NMR spectroscopy. In the meantime, a family of tetraaza macrocyclic chiral solvating agents (TAMCSAs) 1a-1d has been synthesized from D-phenylalanine and (1S,2S)-(+)-1,2-diaminocyclohexane. Discrimination of enantiomers of (+/-)-G1-G9 was carried out in the presence of TAMCSAs 1a-1d by H-1 NMR spectroscopy. The results indicate that enantiomers of (+)-G1-G9 can be effectively discriminated in the presence of TAMCSAs 1a-1d by H-1 NMR signals of multiple protons exhibiting nonequivalent chemical shifts (Delta Delta delta) up to 0.616 ppm. Furthermore, enantiomers of (+/-)-G1-G9 were easily assigned by comparing H-1 NMR signals of the split corresponding protons with those attributed to a single enantiomer. Different optical purities (ee up to 90%) of G1 were clearly observed and calculated in the presence of TAMCSAs 1a-1d, respectively. Intermolecular hydrogen bonding interactions were demonstrated through theoretical calculations of enantiomers of (+/-)-G1 with TAMCSA 1a by means of the hybrid functional theory with the standard basis sets of 3-21G of the Gaussian 03 program.
引用
收藏
页码:13874 / 13887
页数:14
相关论文
共 65 条
[31]   A Simple Method for the Determination of Enantiomeric Excess and identity of Chiral Carboxylic Acids [J].
Joyce, Leo A. ;
Maynor, Marc S. ;
Dragna, Justin M. ;
da Cruz, Gabriella M. ;
Lynch, Vincent M. ;
Canary, James W. ;
Anslyn, Eric V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (34) :13746-13752
[32]   SYNTHESIS OF NITROGEN-CONTAINING MACROCYCLES WITH REDUCTIVE INTRAMOLECULAR COUPLING OF AROMATIC DIIMINES [J].
KISE, N ;
OIKE, H ;
OKAZAKI, E ;
YOSHIMOTO, M ;
SHONO, T .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :3980-3992
[33]   Discrimination of α-Amino Acids Using Green Tea Flavonoid (-)-Epigallocatechin Gallate as a Chiral Solvating Agent [J].
Kumari, Divya ;
Bandyopadhyay, Prasun ;
Suryaprakash, N. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06) :2373-2378
[34]   Chiral Sensing by Nonchiral Tetrapyrroles [J].
Labuta, Jan ;
Hill, Jonathan P. ;
Ishihara, Shinsuke ;
Hanykova, Lenka ;
Ariga, Katsuhiko .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (03) :521-529
[35]   NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers [J].
Labuta, Jan ;
Ishihara, Shinsuke ;
Sikorsky, Tomas ;
Futera, Zdenek ;
Shundo, Atsuomi ;
Hanykova, Lenka ;
Burda, Jaroslav V. ;
Ariga, Katsuhiko ;
Hill, Jonathan P. .
NATURE COMMUNICATIONS, 2013, 4
[36]   New C2-symmetric 2,2′-bipyridine crown macrocycles for enantioselective recognition of amino acid derivatives [J].
Lee, CS ;
Teng, PF ;
Wong, WL ;
Kwong, HL ;
Chan, ASC .
TETRAHEDRON, 2005, 61 (33) :7924-7930
[37]   Enantiodiscrimination of carboxylic acids using the diphenylprolinol NMR chiral solvating agents [J].
Li, Gaowei ;
Cao, Jiangming ;
Zong, Wen ;
Lei, Xinxiang ;
Tan, Renxiang .
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (01) :96-102
[38]   Chiral Primary Amine-Polyoxometalate Acid Hybrids as Asymmetric Recoverable Iminium-Based Catalysts [J].
Li, Jiuyuan ;
Li, Xin ;
Zhou, Pengxin ;
Zhang, Long ;
Luo, Sanzhong ;
Cheng, Jin-Pei .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (26) :4486-4493
[39]   Highly Enantioselective Recognition of Structurally Diverse α-Hydroxycarboxylic Acids using a Fluorescent Sensor [J].
Liu, Hai-Lin ;
Peng, Qian ;
Wu, Yun-Dong ;
Chen, Di ;
Hou, Xue-Long ;
Sabat, Michal ;
Pu, Lin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (03) :602-606
[40]   Separation of enantiomers: needs, challenges, perspectives [J].
Maier, NM ;
Franco, P ;
Lindner, W .
JOURNAL OF CHROMATOGRAPHY A, 2001, 906 (1-2) :3-33