Preparation and Reactions of Optically Active Cyanohydrins Derived from 4- Chlorobenzaldehyde, Cyclohexanone and 2- Methylcyclohexanone using the (R) Hydroxynitrile lyase from Pru - Egyptian Knowledge Bank

1262

Preparation and Reactions of Optically Active Cyanohydrins Derived from 4- Chlorobenzaldehyde, Cyclohexanone and 2- Methylcyclohexanone using the (R) Hydroxynitrile lyase from Pru

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Last updated: 01 Jan 2025

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Abstract

CYANURATION of 4-chlorobenzaldehyde (1), cyclohexanone (2a) and 2-methylcyclo- hexanone (2b) yielded the racemic 2-hydroxy-2-(4-chlorophenyl)ethanenitrile (R,S)-3, cyclohexanone cyanohydrin 21a and (R,S)-2-methylcyclohexanone cyanohydrin (R,S)-21b. The same reaction can be completed by using acetone cyanohydrin (4) as a transcyanating agent. The optically active cyanohydrins (R)-3 and (R)-21b could be respectively obtained by hydrocyanation of 1 and 2b using (R)-hydroxynitrile lyase (R) PaHNL [EC 4.1.2.10] from almonds (Prunus amygdalus) as a chiral catalyst. Cyanohydrins 3 and 21 in their racemic and optically active forms undergo a number of transformations which involve either the hydroxyl group or the cyanide function. Moreover, derivatization of 3 and 21b with (S)-Naproxen chloride (S)-7 gave the respective diastereoisomers 8 and 22b. The optical activities of (R)-3 and 21b as well as their derivatives were recorded. The postulated structures of the new products were supported with compatible elementary and spectroscopic (IR, 1H NMR, 13C NMR, MS and X-ray crystallography) analyses. The antitumor activity of some selected racemic new products and their respective optically active analogues were undertaken. The structure-activity relationship (SAR) was also discussed.

DOI

10.21608/ejchem.2010.1262

Keywords

antitumor activity, Carbonyl compounds, Cyanohydrins, Enzymes and Stereochemistry

Volume

Article Issue

Related Issue

292

Issue Date

2010-10-01

Receive Date

2010-12-02

Publish Date

2010-10-31

Page Start

745

Page End

775

Print ISSN

0449-2285

Online ISSN

2357-0245

Article File

EJCHEM_Volume 53_Issue 5_Pages 745-775.pdf

PDF . 725.1kB

Link

https://ejchem.journals.ekb.eg/article_1262.html

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https://ejchem.journals.ekb.eg/service?article_code=1262

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Type Code

292

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Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

Preparation and Reactions of Optically Active Cyanohydrins Derived from 4- Chlorobenzaldehyde, Cyclohexanone and 2- Methylcyclohexanone using the (R) Hydroxynitrile lyase from Prunus amygdalus

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