Enantioselective lactate binding by chiral tripodal anion hosts derived from amino acids

被引：19

作者：

Barnard, Anna ^{[1
]}

Dickson, Sara Jane ^{[1
]}

Paterson, Martin J. ^{[2
]}

Todd, Adam M. ^{[1
]}

Steed, Jonathan W. ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Durham DH1 3LE, England

[2] Heriot Watt Univ, Sch Engn & Phys Sci, Edinburgh EH14 4AS, Midlothian, Scotland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 08期

基金：

英国工程与自然科学研究理事会;

关键词：

ELECTROSTATIC INTERACTIONS; RESTRICTED CONFORMATIONS; RECEPTORS; DESIGN; RECOGNITION; FLYTRAP; CATIONS; RUTHENIUM(II); CONSTRUCTION; LUMINESCENT;

D O I：

10.1039/b817889e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral, tripodal anion hosts derived from either S-phenylalanine or S-leucine bind D-lactate enantioselectively. The nature of the host-guest interaction has been probed by solution NMR methods and by DFT calculations. The calculations suggest that the D-lactate may form an additional hydrogen bond in the host-guest complex while the L-lactate complex contains an intramolecular hydrogen bond. Anion binding is in competition with host dimerisation, as demonstrated by DOSY and H-1 NMR spectroscopy, and DFT calculations.

引用

页码：1554 / 1561

页数：8

共 50 条

[31] Chiral Amino Acids-Derived Catalysts and Ligands
Liu, Xiaohua
Dong, Shunxi
Lin, Lili
Feng, Xiaoming
CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (09) : 791 - 797
[32] Synthesis of α-Amino Acids Based on Chiral Tricycloiminolactone Derived from Natural (+)-Camphor
Luo, Yong-Chun
Zhang, Huan-Huan
Wang, Yao
Xu, Peng-Fei
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (10) : 1317 - 1330
[33] Chiral Imidazolium Salts Derived from Amino Acids: Synthesis Characterization and Structure
Quinonez-Lopez, Raul R.
Idalia Rangel-Salas, I.
Roberto Estrada-Flores, J.
Cortes-Llamas, Sara A.
Gallegos-Castillo, Saul
CURRENT ORGANIC CHEMISTRY, 2018, 22 (26) : 2589 - 2597
[34] A new class of chiral diimine ligands derived from amino acids.
Morgan, RJ
Dillon, J
Morgan, O
Donovan, RJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U1025 - U1025
[35] Enantioselective recognition of carboxylates:: A receptor derived from α-aminoxy acids functions as a chiral shift reagent for carboxylic acids
Yang, D
Li, X
Fan, YF
Zhang, DW
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) : 7996 - 7997
[36] Modular ligands derived from amino acids for the enantioselective addition of organozinc reagents to aldehydes
Richmond, ML
Seto, CT
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19): : 7505 - 7508
[37] A new chiral disulfonamide ligand derived from a-amino acid for catalytic enantioselective cyclopropanation
Tetrahedron Lett, 8 (1423):
[38] Enantioselective synthesis of amino acids from ammonia
Li, Mao-Lin
Pan, Jia-Bin
Zhou, Qi-Lin
NATURE CATALYSIS, 2022, 5 (06) : 571 - +
[39] Enantioselective synthesis of amino acids from ammonia
Mao-Lin Li
Jia-Bin Pan
Qi-Lin Zhou
Nature Catalysis, 2022, 5 : 571 - 577
[40] Enantioselective synthesis of α-amino acids from nitroalkenes
Sabelle, S
Lucet, D
Le Gall, T
Mioskowski, C
TETRAHEDRON LETTERS, 1998, 39 (15) : 2111 - 2114

← 1 2 3 4 5 →