Synthesis of Optically Active γ- and δ-Lactones by Microbiological Reduction

Muys, G. Tuynenburg; Ven, B. van der; Jonge, A. P. de

doi:10.1038/194995b0

Search citation statements

Order By: Relevance

Paper Sections

Select...

Introduction2

Enantioselecttvity In Enzymatic Reactions1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1963

2019

Publication Types

Select...

Article9

Other1

Relationship

Self Cite0

Independent10

Authors

Journals

Cited by 41 publications

(7 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, yeasts have been known to be able to reduce a ketone to an alcohoI. 15 ) Consequently, y-dodecalactone may be formed also from lO-ketostearic acid existing in the crude lO-hydroxystearic acid. We are investigating these conversion pathways.…”

mentioning

confidence: 99%

Biotransformation of Oleic Acid to Optically Activeγ-Dodecalactone

Gocho¹,

Tabogami²,

Inagaki³

et al. 1995

Bioscience, Biotechnology, and Biochemistry

View full text Add to dashboard Cite

mentioning

confidence: 99%

Biotransformation of Oleic Acid to Optically Activeγ-Dodecalactone

Gocho¹,

Tabogami²,

Inagaki³

et al. 1995

Bioscience, Biotechnology, and Biochemistry

View full text Add to dashboard Cite

“…In the case of microbial synthesis of optically active 7-and 8-lactones from 4(5)-oxoalkanoic acids (75), increasing enantioselectivity in favor of 4R(5R)-configurated lactones should be expected by elongation of the alkyl side chain. The chirospecific analysis of 7(6)-lactones (55) is of some interest with respect to their importance as flavor constituents of many fruits and other foodstuffs such as dairy products.…”

Section: Enantioselecttvity In Enzymatic Reactionsmentioning

confidence: 99%

Chirality in flavor chemistry‐recent developments in synthesis and analysis

Mosandl

1988

Food Reviews International

View full text Add to dashboard Cite

The state of the art in research on chirality and odor is presented, with special emphasis on synthetic and analytical methods. The syntheses of l-octen-3-ol enantiomers, of chiral alkan-2-yl esters, of "whisky lactone," and of chiral sulfur compounds, known as characteristic components of the yellow passion fruit, are reviewed. It is demonstrated that optically pure stereoisomers exhibit their own, specific sensory characteristics. Therefore, stereoisomers of very high enantiomeric excess (ee) must be achieved for valid evaluations of their structure-function relationships. Analytical methods for stereodifferentiation of chiral flavor compounds and recent developments in biotechnology are discussed.

show abstract

“…If the other enantiomer is needed, efforts have to be devoted to obtain it by acting on the choice of the biocatalyst or on the structure of the starting substrate. In the case of secondary alcohols, derived from the reduction of a prochiral ketone, useful results were obtained by growing cultures from different strains of the same microorganism [5], or using different microorganisms on the same substrate [6][7][8] or the same microorganism on modified substrates [9].…”

Section: Introductionmentioning

confidence: 99%