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Literature DB >> 18989929

A simple microscale method for determining the relative stereochemistry of statine units.

Abstract

A simple method to determine the relative stereochemistry of statine amino acids (gamma-amino-beta-hydroxyacids) by using (1)H NMR spectroscopy is described. Configurational assignment of statine units within complex natural products is possible without degradation or derivatization as the syn and anti diastereomers can be distinguished by using a combination of chemical shift and coupling constant information derived from the alpha-methylene ABX system. Seventy-three examples are provided, demonstrating the scope and limitations of the methodology. These examples range in complexity from simple statine units to cyclic depsipeptides, such as tamandarin B.

Entities: Chemical Gene Species

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Year: 2008 PMID： 18989929 PMCID： PMC2765571 DOI： 10.1021/jo8012429

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

22 in total

1. Toward creation of a universal NMR database for the stereochemical assignment of acyclic compounds: proof of concept.

Authors: J Lee; Y Kobayashi; K Tezuka; Y Kishi
Journal: Org Lett Date: 1999-12-30 Impact factor: 6.005

2. One-Pot Sequential Asymmetric Hydrogenation Utilizing Rh(I) and Ru(II) Catalysts.

Authors: Takayuki Doi; Masaya Kokubo; Keiji Yamamoto; Takashi Takahashi
Journal: J Org Chem Date: 1998-02-06 Impact factor: 4.354

3. Molecular docking and 3D-QSAR studies on the binding mechanism of statine-based peptidomimetics with beta-secretase.

Authors: Zhili Zuo; Xiaomin Luo; Weiliang Zhu; Jianhua Shen; Xu Shen; Hualiang Jiang; Kaixian Chen
Journal: Bioorg Med Chem Date: 2005-03-15 Impact factor: 3.641

Review 4. Phytochemistry in the microgram domain - a LC-NMR perspective.

Authors: Jean-Luc Wolfender; Emerson F Queiroz; Kurt Hostettmann
Journal: Magn Reson Chem Date: 2005-09 Impact factor: 2.447

5. Total syntheses and biological investigations of tamandarins A and B and tamandarin A analogs.

Authors: B Liang; D J Richard; P S Portonovo; M M Joullié
Journal: J Am Chem Soc Date: 2001-05-16 Impact factor: 15.419

6. Stereochemical Determination of Acyclic Structures Based on Carbon-Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural Products.

Authors: Nobuaki Matsumori; Daisuke Kaneno; Michio Murata; Hideshi Nakamura; Kazuo Tachibana
Journal: J Org Chem Date: 1999-02-05 Impact factor: 4.354

7. The isolation and structure elucidation of Tasiamide B, a 4-amino-3-hydroxy-5-phenylpentanoic acid containing peptide from the marine Cyanobacterium Symploca sp.

Authors: Philip G Williams; Wesley Y Yoshida; Richard E Moore; Valerie J Paul
Journal: J Nat Prod Date: 2003-07 Impact factor: 4.050

8. Statine and its derivatives. Conformational studies using nuclear magnetic resonance spectrometry and energy calculations.

Authors: D H Rich; Y Terada; M Kawai
Journal: Int J Pept Protein Res Date: 1983-09

9. An NMR method for assigning relative stereochemistry to beta-hydroxy ketones deriving from aldol reactions of methyl ketones.

Authors: William R Roush; Thomas D Bannister; Michael D Wendt; Michael S VanNieuwenhze; Darin J Gustin; Garrett J Dilley; Gregory C Lane; Karl A Scheidt; William J Smith
Journal: J Org Chem Date: 2002-06-14 Impact factor: 4.354

10. Marine natural product libraries for high-throughput screening and rapid drug discovery.

Authors: Tim S Bugni; Burt Richards; Leen Bhoite; Daniel Cimbora; Mary Kay Harper; Chris M Ireland
Journal: J Nat Prod Date: 2008-05-28 Impact factor: 4.050

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Authors: Fatma H Al-Awadhi; Brian K Law; Valerie J Paul; Hendrik Luesch
Journal: J Nat Prod Date: 2017-10-31 Impact factor: 4.050

Review 2. Life in cellulose houses: symbiotic bacterial biosynthesis of ascidian drugs and drug leads.

Authors: Eric W Schmidt; Mohamed S Donia
Journal: Curr Opin Biotechnol Date: 2010-11-01 Impact factor: 9.740

3. Cytotoxic halogenated macrolides and modified peptides from the apratoxin-producing marine cyanobacterium Lyngbya bouillonii from Guam.

Authors: Susan Matthew; Lilibeth A Salvador; Peter J Schupp; Valerie J Paul; Hendrik Luesch
Journal: J Nat Prod Date: 2010-09-24 Impact factor: 4.050