Assignment of the Absolute Configuration of Concentricolide - Absolute Configuration Determination of Its Bioactive Analogs Using DFT Methods

被引：35

作者：

Ren, Jie ^{[2
]}

Jiang, Ju-Xing ^{[2
,3
]}

Li, Liang-Bo ^{[2
,3
]}

Liao, Tou-Geng ^{[2
,3
]}

Tian, Ren-Rong ^{[1
]}

Chen, Xu-lin ^{[1
]}

Jiang, Si-Ping ^{[4
]}

Pittman, Charles U., Jr. ^{[5
]}

Zhu, Hua-Jie ^{[2
]}

机构：

[1] Chinese Acad Sci, Wuhan Inst Virol, State Key Lab Virol, Wuhan 430071, Peoples R China

[2] Chinese Acad Sci, Organ Synth & Nat Prod Lab, State Key Lab Phytochem & Plant Resources W China, Kunming Inst Bot, Kunming 650204, Peoples R China

[3] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

[4] Tibetan Plateau Inst Biol, Tibet 850001, Peoples R China

[5] Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 23期

基金：

中国国家自然科学基金;

关键词：

Configuration determination; Biological activity; Density functional calculations; Chirality; Circular dichroism; VIBRATIONAL CIRCULAR-DICHROISM; COUPLED-CLUSTER CALCULATIONS; OPTICAL-ROTATORY DISPERSION; 1ST ENANTIOMERICALLY PURE; DENSITY-FUNCTIONAL THEORY; AB-INITIO CALCULATION; ENANTIOSELECTIVE ADDITION; MOLECULAR-STRUCTURE; RECENT PROGRESS; ROTATION;

D O I：

10.1002/ejoc.200900422

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The configuration of concentricolide was assigned as (S). The configuration of its three analogs, which have anti-HIV-1 activity, were predicted by optical rotation values obtained by the B3LYP/aug-cc-pVDZ//B3LYP/6-31+G(d) and B3LYP/aug-cc-pVDZ//MP2/6-311+G(d) methods. The two methods predict very close optical rotation magnitudes for all three chiral analogs of concentricolide. The two methods were applied in optical rotation predictions for seven other concentricolide analogs. Circular dichroism calculations were performed for four of the seven analogs at the B3LYP/aug-cc-pVDZ level. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：3987 / 3991

页数：5

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