Determination of the absolute configuration of a secondary alcohol by NMR spectroscopy using difluorodinitrobenzene

Harada, Kenichi; Shimizu, Youhei; Kawakami, Atsuko; Fujii, Kiyonaga

doi:10.1016/s0040-4039(99)01926-7

Cited by 12 publications

(12 citation statements)

References 8 publications

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“…19) Surprisingly, this structure is closely similar to that of scytoneamine A isolated from a marine cyanobacterium Scytonema. 35) There are many b-amino acid-containing peptides from cyanobacteria.…”

Section: B B-amino Acid Containing Peptides From Cyanobacteriamentioning

confidence: 61%

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Production of Secondary Metabolites by Freshwater Cyanobacteria

Harada

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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Freshwater cyanobacteria produce lethal toxins such as microcystins and anatoxins. During the purification of microcystins in bloom samples we found that a toxic cyanobacterium produced not only microcystins but also other types-peptides in early 1990. Since then we have isolated approximately thirty peptides from freshwater cyanobacteria. In this manuscript we focused on the following topics concerning the isolated peptides: 1) how to isolate desired compounds and to determine their structures, 2) structural classification of isolated compounds, 3) isolation of similar peptides from laboratory strains and bloom materials, 4) structurally related peptides from freshwater and marine origins, 5) b b-amino acid containing peptides from cyanobacteria, 6) comprehensive analysis system for the biosynthetic study of peptides produced by cyanobacteria, 7) biological activities of isolated compounds.

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Section: B B-amino Acid Containing Peptides From Cyanobacteriamentioning

confidence: 61%

“…Naturally, we have to determine the stereochemistry of these two secondary alcohols and we are also developing an effective method for secondary alcohols. 19,20) Through the present study about 30 compounds were isolated, almost of which are peptides and determined their 892 Vol. 52, No.…”

Section: How To Isolate Desired Compounds and To Determine Their Strumentioning

confidence: 96%

Production of Secondary Metabolites by Freshwater Cyanobacteria

Harada

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…21 The DFDNB is first reacted with the alcohol and then with enantiomerically pure 1-phenylethylamine. 21 The DFDNB is first reacted with the alcohol and then with enantiomerically pure 1-phenylethylamine.…”

Section: Chiral Reagents For Determining Ee and Acmentioning

confidence: 99%

Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy

2003

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“…The AC of sec-alcohols could be determined through a scheme involving the use of 1,5-difluoro-2,4-dinitrobenzene (DFDNB). 21 The DFDNB is first reacted with the alcohol and then with enantiomerically pure 1-phenylethylamine. The conformations of the two diastereomers of a chiral alcohol are fixed by the plane of the dinitrobenzene ring in the derivative, thereby enabling the assignment of AC.…”

Section: Chiral Reagents For Determining Ee and Acmentioning

confidence: 99%

Chiral Reagents for the Determination of Enantiomeric Excess and Absolute Configuration Using NMR Spectroscopy

Wenzel

Wilcox

2003

ChemInform

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Recent advances in the development of chiral derivatizing and solvating agents that facilitate the determination of enantiomeric excess and absolute configuration are reviewed. These include metal-containing species, host-guest systems, donoracceptor compounds, and liquid crystal discriminating agents. In the aggregate, these reagents can be used to analyze a wide range of compound classes. Chirality 15: 256-270, 2003.

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Determination of the absolute configuration of a secondary alcohol by NMR spectroscopy using difluorodinitrobenzene

Cited by 12 publications

References 8 publications

Production of Secondary Metabolites by Freshwater Cyanobacteria

Production of Secondary Metabolites by Freshwater Cyanobacteria

Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy

Chiral Reagents for the Determination of Enantiomeric Excess and Absolute Configuration Using NMR Spectroscopy

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