scholarly journals Concise Synthesis of Catechin Metabolites 5-(3′,4′-Dihydroxyphenyl)-γ-valerolactones (DHPV) in Optically Pure Form and Their Stereochemical Effects on Skin Wrinkle-Reducing Activities

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1970 ◽  
Author(s):  
Joonseong Hur ◽  
A-Ram Kim ◽  
Hyun Su Kim ◽  
Changjin Lim ◽  
Taewoo Kim ◽  
...  
Keyword(s):  
Pure Form ◽  
Synthetic Route ◽  
Enantiomerically Pure ◽  
Efficient Construction ◽  
Optically Pure

A concise and scalable synthetic route for optically pure (4S) and (4R)-5-(3′,4′-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexenol. Noticeably, the different skin wrinkle-reducing activities of each metabolite were revealed via our unique syntheses of DHPVs in an enantiomerically pure form.

scholarly journals Altering the Stereoselectivity of Whole-Cell Biotransformations via the Physicochemical Parameters Impacting the Processes

Catalysts ◽  
2021 ◽  
Vol 11 (7) ◽  
pp. 781
Author(s):  
Agnieszka Raczyńska ◽  
Joanna Jadczyk ◽  
Małgorzata Brzezińska-Rodak
Keyword(s):  
Culture Conditions ◽  
Biologically Active ◽  
Enantiomerically Pure ◽  
Whole Cells ◽  
Chiral Compounds ◽  
Physicochemical Factors ◽  
Pure Compounds ◽  
Genetic Level ◽  
Prochiral Ketones ◽  
Optically Pure

The enantioselective synthesis of organic compounds is one of the great challenges in organic synthetic chemistry due to its importance for the acquisition of biologically active derivatives, e.g., pharmaceuticals, agrochemicals, and others. This is why biological systems are increasingly applied as tools for chiral compounds synthesis or modification. The use of whole cells of “wild-type” microorganisms is one possible approach, especially as some methods allow improving the conversion degrees and controlling the stereoselectivity of the reaction without the need to introduce changes at the genetic level. Simple manipulation of the culture conditions, the form of a biocatalyst, or the appropriate composition of the biotransformation medium makes it possible to obtain optically pure products in a cheap, safe, and environmentally friendly manner. This review contains selected examples of the influence of physicochemical factors on the stereochemistry of the biocatalytic preparation of enantiomerically pure compounds, which is undertaken through kinetically controlled separation of their racemic mixtures or reduction of prochiral ketones and has an effect on the final enantiomeric purity and enantioselectivity of the reaction.

ChemInform Abstract: Short Synthetic Route to the Enantiomerically Pure (R)-(+)-γ- Decalactone.

ChemInform ◽  
2010 ◽  
Vol 28 (1) ◽  
pp. no-no
Author(s):  
J. KULA ◽  
M. SIKORA ◽  
H. SADOWSKA ◽  
J. PIWOWARSKI
Keyword(s):  
Synthetic Route ◽  
Enantiomerically Pure

Convenient Synthetic Route to an Enantiomerically Pure FMOC α-Amino Acid

2008 ◽  
Vol 73 (23) ◽  
pp. 9334-9339 ◽  
Author(s):  
Douglass F. Taber ◽  
James F. Berry ◽  
Timothy J. Martin
Keyword(s):  
Amino Acid ◽  
Synthetic Route ◽  
Enantiomerically Pure

Simple and efficient synthesis of allo- and threo-3,3′-dimethylcystine derivatives in enantiomerically pure form

2008 ◽  
Vol 19 (12) ◽  
pp. 1425-1429 ◽  
Author(s):  
R.B. Nasir Baig ◽  
V. Sai Sudhir ◽  
Srinivasan Chandrasekaran
Keyword(s):  
Pure Form ◽  
Efficient Synthesis ◽  
Enantiomerically Pure

A Rapid and Simple Chromatographic Separation of Diastereomers of Silibinin and Their Oxidation to Produce 2,3-Dehydrosilybin Enantiomers in an Optically Pure Form

Planta Medica ◽  
2013 ◽  
Vol 79 (12) ◽  
pp. 1077-1080 ◽  
Author(s):  
Giovanni Di Fabio ◽  
Valeria Romanucci ◽  
Cinzia Di Marino ◽  
Lorenzo De Napoli ◽  
Armando Zarrelli
Keyword(s):  
Chromatographic Separation ◽  
Pure Form ◽  
Separation Of Diastereomers ◽  
Optically Pure

Chemoenzymatic synthesis of antiinflammatory drugs in enantiomerically pure form

2000 ◽  
Vol 11 (11) ◽  
pp. 2403-2407 ◽  
Author(s):  
Amit Basak ◽  
Ahindra Nag ◽  
Gautam Bhattacharya ◽  
Subrata Mandal ◽  
Sikha Nag
Keyword(s):  
Pure Form ◽  
Chemoenzymatic Synthesis ◽  
Antiinflammatory Drugs ◽  
Enantiomerically Pure
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