Efficient Determination of the Enantiomeric Purity and Absolute Configuration of Flavanones by Using (S)-3,3′-Dibromo-1,1′-bi-2-naphthol as a Chiral Solvating Agent

被引：17

作者：

Du, Guoxin ^{[1
,2
]}

Li, Yisu ^{[2
,3
]}

Ma, Shunan ^{[1
]}

Wang, Rui ^{[1
]}

Li, Bo ^{[2
]}

Guo, Fujiang ^{[1
]}

Zhu, Weiliang ^{[2
]}

Li, Yiming ^{[1
]}

机构：

[1] Shanghai Univ Tradit Chinese Med, Sch Pharm, Shanghai 201203, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China

[3] Univ Sci & Technol China, Nano Sci & Technol Inst, Suzhou 215123, Peoples R China

来源：

JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 12期

基金：

中国国家自然科学基金; 国家高技术研究发展计划(863计划);

关键词：

CIRCULAR-DICHROISM; NMR ANALYSIS; SHIFT-REAGENT; ASSIGNMENT; ENANTIODIFFERENTIATION; DISCRIMINATION; PROTOCOLS; ACIDS;

D O I：

10.1021/acs.jnatprod.5b00690

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The enantiomeric purity and absolute configuration of flavanones were first determined using (S)-3,3'-dibromo-1,1'-bi-2-naphthol as a chiral solvating agent by means of H-1 NMR spectroscopy. The enantiomeric purity results closely matched those based on chiral HPLC analysis.

引用

页码：2968 / 2974

页数：7

共 33 条

[1]

ANTUS S, 1994, LIEBIGS ANN CHEM, P497

[2] NMR method for determination of enantiomeric purity of sulfinimines [J].

Ardej-Jakubisiak, Monika ;

Kawecki, Robert .

TETRAHEDRON-ASYMMETRY, 2008, 19 (23) :2645-2647

[3] Determination of levamisole and tetramisole in seized cocaine samples by enantioselective high-performance liquid chromatography and circular dichroism detection [J].

Bertucci, Carlo ;

Tedesco, Daniele ;

Fabini, Edoardo ;

Di Pietra, Anna Maria ;

Rossi, Francesca ;

Garagnani, Marco ;

Del Borrello, Elia ;

Andrisano, Vincenza .

JOURNAL OF CHROMATOGRAPHY A, 2014, 1363 :150-154

[4] Assignment of the absolute configuration of hydroxy- and aminophosphonates by NMR spectroscopy [J].

Blazewska, Katarzyna M. ;

Gajda, Tadeusz .

TETRAHEDRON-ASYMMETRY, 2009, 20 (12) :1337-1361

[5] Enantiodifferentiation of promethazine using (S)-(-)-BINOL as the NMR chiral solvating agent: determination of the enantiomeric purity and performance comparison with traditional chiral HPLC [J].

Borowiecki, Pawel .

TETRAHEDRON-ASYMMETRY, 2015, 26 (01) :16-23

[6] Ternary ion-pair complexation: a protocol for chiral discrimination and the assignment of absolute configuration of chiral hydroxy acids [J].

Chaudhari, Sachin R. ;

Suryaprakash, N. .

NEW JOURNAL OF CHEMISTRY, 2013, 37 (12) :4025-4030

[7] Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding [J].

Chin, J ;

Kim, DC ;

Kim, HJ ;

Panosyan, FB ;

Kim, KM .

ORGANIC LETTERS, 2004, 6 (15) :2591-2593

[8] Enantio-differentiation of O-heterocycles using a binol-derived disulfonimide as a chiral solvating agent [J].

Couffin, A. ;

du Boullay, O. Thillaye ;

Vedrenne, M. ;

Navarro, C. ;

Martin-Vaca, B. ;

Bourissou, D. .

CHEMICAL COMMUNICATIONS, 2014, 50 (45) :5997-6000

[9] Separation and peroxisome proliferator-activated receptor-γ agonist activity evaluation of synthetic racemic bavachinin enantiomers [J].

Du, Guoxin ;

Feng, Li ;

Yang, Zhuo ;

Shi, Jiye ;

Huang, Cheng ;

Guo, Fujiang ;

Li, Bo ;

Zhu, Weiliang ;

Li, Yiming .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (12) :2579-2583

[10] In tube determination of the absolute configuration of α- and β-hydroxy acids by NMR via chiral BINOL borates [J].

Freire, Felix ;

Quinoa, Emilio ;

Riguera, Ricardo .

CHEMICAL COMMUNICATIONS, 2008, (35) :4147-4149

← 1 2 3 4 →