Enzymatic synthesis of (R)-cyanohydrins by three (R)-oxynitrilase sources in micro-aqueous organic medium

Lin, Guo‐Qiang; Han, Shiqing; Li, Zu‐Yi

doi:10.1016/s0040-4020(98)01160-0

Cited by 55 publications

(35 citation statements)

References 16 publications

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“…All analyses were performed isothermally. The temperature programs and retention times are: The absolute configuration of 1a was determined by comparison with optical rotation [22] and elution order of the enantiomers (as their TMS ethers) by enantioselective GC. [23,24] Conversion of the enantiopure acetate to its TMS ether was performed according to a procedure from the literature.…”

Section: Experimental Section Materials and Methodsmentioning

confidence: 99%

Hydrolase‐Catalysed Preparation of Chiral α,α‐Disubstituted Cyanohydrin Acetates

et al. 2007

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The enzymatic hydrolysis of esters of tertiary alcohols has long been a challenge. In particular their kinetic resolutions have virtually not been addressed. Here we describe the successful kinetic resolution of a,a-disubstituted cyanohydrin acetates, a type of protected tertiary alcohols that form particularly interesting building blocks in organic synthesis. Utilising Subtilisin A the hydrolysis reaction was (S)-selective, while Candida rugosa lipase was (R)-selective. With these commercially available enzymes both enantiomers of the a,a-disubstituted cyanohydrin acetates are now accessible.

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Section: Experimental Section Materials and Methodsmentioning

confidence: 99%

Hydrolase‐Catalysed Preparation of Chiral α,α‐Disubstituted Cyanohydrin Acetates

et al. 2007

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“…L.) in micoaqueous organic medium, although the enzyme activity and other properties are not clear. 30) Thus, we discovered new producers of HNL of plant origin, while less than 20 plants have been reported to be the producers of HNLs in the long history of the enzymology of HNLs. These results show that the newly discovered HNLs have the potential of application in the asymmetric synthesis of optically active cyanohydrins.…”

Section: Discussionmentioning

confidence: 99%

Screening for New Hydroxynitrilases from Plants

Asano

Tamura

Doi

et al. 2005

Bioscience, Biotechnology, and Biochemistry

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We established a simple HPLC method to determine the activity and stereochemistry of the chiral mandelonitrile synthesized from benzaldehyde and cyanide, and applied it to screen for hydroxynitrile lyase (HNL) activity of plant origin. A total of 163 species of plants among 74 families were examined for (R)-and (S)-HNL activities using the method. We discovered that homogenate of leaves of Baliospermum montanum shows (S)-HNL activity, while leaves and seeds from Passiflora edulis, and seeds from Eriobotrya japonica, Chaenomles sinensis, Sorbus aucuparia, Prunus mume, and Prunus persica show (R)-HNL activity. Partially purified (R)-HNLs from Passiflora edulis and Eriobotrya japonica acted not only on benzaldehyde but also on aliphatic ketone. The enantiomeric excess of (R)-methylpropylketone cyanohydrin synthesized from 2-pentanone using homogenate from leaves of Passiflora edulis was 87.0%, and that of (R)-mandelonitrile synthesized by homogenate from seeds of Eriobotrya japonica was 85.0%.

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“…Almonds provide a rich source of this enzy me [2,[19][20][21][22][23]. Thus, for examp le, co mpound (R)-2b was obtained with enantio meric excess value (ee %) of 91 % ( 1 H NM R) and a specific rotation value [α] D/25 of + 38.4 (c 0.01666, acetone).…”

Section: Chemistry Synthesis Of the Optically Active Cyanohydrins 2a-dmentioning

confidence: 99%

“…The enantioselective preparation of optically pure cyanohydrins is catalytically developed by making use of cyclic dipeptides [9], nanocrystalline magnesium o xide [15] and various chiral co mplexes of titaniu m [16], alu minu m [17] and boron [18]. Besides, it can be enzymatically cataly zed by means of hydro xynitrile lyases (o xynitrilases) extracted fro m plant sources [2,4,19]. This approach is rather decisive, clean and cheap [5,[20][21][22][23].…”

mentioning

confidence: 99%

Preparation and Reactions of Certain Racemic and Optically Active Cyanohydrins Derived from 2-Chlorobenzaldehyde, 4-Fluorobenzaldehyde, Benzo[d][1,3]-dioxole-5-carbaldehyde and 2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde. Antimicrobial and in vitro Antitumor Evaluation of the Products

2017

Egypt. J. Chem.

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Enzymatic synthesis of (R)-cyanohydrins by three (R)-oxynitrilase sources in micro-aqueous organic medium

Cited by 55 publications

References 16 publications

Hydrolase‐Catalysed Preparation of Chiral α,α‐Disubstituted Cyanohydrin Acetates

Hydrolase‐Catalysed Preparation of Chiral α,α‐Disubstituted Cyanohydrin Acetates

Screening for New Hydroxynitrilases from Plants

Preparation and Reactions of Certain Racemic and Optically Active Cyanohydrins Derived from 2-Chlorobenzaldehyde, 4-Fluorobenzaldehyde, Benzo[d][1,3]-dioxole-5-carbaldehyde and 2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde. Antimicrobial and in vitro Antitumor Evaluation of the Products

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