Characterization of a New (R)-Hydroxynitrile Lyase from the Japanese ApricotPrunus mumeand cDNA Cloning and Secretory Expression of One of the Isozymes inPichia pastoris

Fukuta, Yasuhisa; Nanda, Samik; Kato, Yasuo; Yurimoto, Hiroya; Sakai, Yasuyoshi; Komeda, Hidetsugu; Asano, Yasuhisa

doi:10.1271/bbb.100187

Cited by 29 publications

(22 citation statements)

References 30 publications

(40 reference statements)

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“…S-selective HNL (S-HNL) activity was found in a homogenate of the leaves of Baliospermum montanum, while R-selective HNLs (R-HNLs) were detected in the leaves and seeds of Passiflora edulis, and the seeds of Eriobotrya japonica, Prunus mume, Prunus persica, Chaenomles sinensis and Sorbus aucuparia. The HNLs from E. japonica (EjHNL) (Ueatrongchit et al, 2008(Ueatrongchit et al, , 2009, P. edulis (PeHNL) (Ueatrongchit et al, 2010), P. mume (PmHNL) (Fukuta et al, 2011;Nanda et al, 2005Nanda et al, , 2006, and B. montanum (BmHNL) (Dadashipour et al, 2011) have been purified to homogeneity and their enzymatic properties characterized. PmHNL shows excellent potential for the asymmetric synthesis of cyanohydrins in organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (R)-β-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous–organic biphasic system

Fuhshuku

Asano

2011

Journal of Biotechnology

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Section: Introductionmentioning

confidence: 99%

Synthesis of (R)-β-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous–organic biphasic system

Fuhshuku

Asano

2011

Journal of Biotechnology

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“…Although there has been a preference for acquiring complete eukaryotic HNL sequences via the construction and screening of cDNA libraries,, this type of strategy is labor intensive and time consuming. Instead, we aligned the reported gene sequences of all the HNLs isolated from Prunus species and designed homology primers based on several conserved regions of these genes.…”

Section: Resultsmentioning

confidence: 99%

Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications

Zheng

Wang

et al. 2017

Adv Synth Catal

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Biocatalysts originating from Badamu (Prunusc ommunis)h ave been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile,akey building block of thiamphenicol and florfenicol. Here,f our hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressedi nPichia pastoris.T he biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis.A mong then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasicr eactionc onditions,s eventeen prochi-ral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to > 99.9% ee), which provide af acile access to numerous chiral amino alcohols,h ypoglycemic agents,a ngiotension converting enzyme (ACE)i nhibitors and b-blockers. This workt herefore underlines the importance of discovering the most potent biocatalyst among ag roup of isozymes for converting unnatural substrates into value-added products.

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“…Plants producing amygdalin and/or prunasin and HNLs purified/reported from them are Prunus amygdalus or Prunus dulcis ( Pa HNL), Prunus serotina ( Ps HNL), Prunus lyonii ( Pl HNL), Prunus persica ( Pper HNL), P. amygdalus turcomanica ( Pat HNL), Prunus mume ( Pm HNL), Prunus armeniaca ( Pars HNL), Prunus domestica ( Pd HNL), Prunus laurocerasus ( Pla HNL), P. pseudoarmeniaca ( Pp HNL), Eriobotrya japonica ( Ej HNL), and Passiflora edulis ( Pe HNL). Because both amygdalin and prunasin are present in their R stereomeric form, their hydrolysis produces ( R )‐mandelonitrile, so these HNLs are reported to be R ‐specific.…”

Section: Different Approaches To Discovering Hnlsmentioning

confidence: 99%

Modern Approaches to Discovering New Hydroxynitrile Lyases for Biocatalysis

Padhi

2016

ChemBioChem

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Hydroxynitrile lyases (HNLs) have grown in importance from laboratory to industry due to their potential to catalyze stereoselective C-C bond-formation reactions in the synthesis of several chiral intermediates, such as enantiopure α-cyanohydrins, β-nitro alcohols, and their derivatives with multiple functional groups. With these wide applications, the demand for finding new HNLs has increased, and this has led to exploration not only of new HNLs but also of new ways to discover them. An exclusive review article on HNLs by Asano et al. in 2011 described the discovery of HNLs along with their applications. Since then many scientific advancements have been seen in this area. This article aims to highlight the modern HNL discovery approaches, based mainly on 1) genome mining, 2) use of INTMSAlign software, 3) rational design (based on a millipede HNL), 4) evolution of catalytic mechanisms, 5) protein engineering guided by catalytic mechanisms, and 6) screening of plants with cyanogen glycoside (CG) content. This description is followed by future prospects. Overall this review represents the present state and the future potential of HNL discovery approaches, and so might be hoped to be instrumental not only in exploration of new HNLs but also in the invention of methods for potential biotechnological applications.

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Characterization of a New (R)-Hydroxynitrile Lyase from the Japanese ApricotPrunus mumeand cDNA Cloning and Secretory Expression of One of the Isozymes inPichia pastoris

Cited by 29 publications

References 30 publications

Synthesis of (R)-β-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous–organic biphasic system

Synthesis of (R)-β-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous–organic biphasic system

Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications

Modern Approaches to Discovering New Hydroxynitrile Lyases for Biocatalysis

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