scholarly journals A Study on the Lipase-catalysed Acylation of 6,7-Dihydroxy-linalool

2016 ◽  
Vol 11 (9) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Stefano Serra ◽  
Davide De Simeis
Keyword(s):  
Hydroxy Group ◽  
Candida Rugosa ◽  
Secondary Hydroxy Group ◽  
Acylation Reaction ◽  
Novozyme 435 ◽  
Isomeric Purity ◽  
Reaction Proceeds ◽  
Vegetal Species ◽  
Lipase From Candida Rugosa

We here describe a study of the enzyme-mediated acylation reaction of 6,7-dihydroxy-linalool stereoisomers, which are natural triols occurring in different vegetal species. We found that only few lipases are able to catalyze the acylation of the secondary hydroxy group present in these isomers and only lipase from Candida rugosa and novozyme 435 provide either (3 R,6 R)-6-acetoxy-7-hydroxylinalool or (3 R,6 S)-6-acetoxy-7-hydroxylinalool in moderate and very good isomeric purity, respectively Even for these favorable cases the reaction proceeds very sluggishly. Our finding can give a sensible interpretation to the fact that 6-acyl-7-hydroxy-linalool derivatives do not occur in nature, whereas the corresponding glycosides, whose formation is catalyzed by glycosidase, are very common.

scholarly journals A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols

2018 ◽  
Vol 14 ◽  
pp. 1229-1237
Author(s):  
Anna Czarnecka ◽  
Emilia Kowalska ◽  
Agnieszka Bodzioch ◽  
Joanna Skalik ◽  
Marek Koprowski ◽  
...  
Keyword(s):  
Transition Metal ◽  
Hydroxy Group ◽  
Potential Application ◽  
Selective Removal ◽  
Synthetic Approach ◽  
Secondary Hydroxy Group ◽  
Optoelectronic Materials ◽  
Reaction Proceeds

We present a successful deoxygenation reaction of ortho-1,3-dithianylaryl(aryl)methanols which enables a selective removal of the secondary hydroxy group in presence of the 1,3-dithianyl moiety under reductive conditions. This reaction proceeds well with ZnI2/Na(CN)BH3 in dichloroethane or benzene for both unsubstituted and substituted aryls (by electron-rich groups). This is leading to formyl-protected diarylmethanes with potential application in the synthesis of new pharmaceuticals and optoelectronic materials. This synthetic approach gives an access to a wide variety of functionalized ortho-1,3-dithianylaryl(aryl)methanes in 26–95% yields and is recommended for the substrates containing sulfur atoms, for which transition metal-induced reactions fail.

Immobilization of lipase from Candida rugosa on Sepabeads®: the effect of lipase oxidation by periodates

2011 ◽  
Vol 34 (7) ◽  
pp. 803-810 ◽  
Author(s):  
Nevena Ž. Prlainović ◽  
Zorica D. Knežević-Jugović ◽  
Dušan Ž. Mijin ◽  
Dejan I. Bezbradica
Keyword(s):  
Candida Rugosa ◽  
Lipase From Candida Rugosa

scholarly journals Mechanochemo-enzymatic Synthesis of Aromatic Aldehyde Oxime Esters

2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300
Author(s):  
Margarita A. Arthur-Santiago ◽  
Rosa María Oliart-Ros ◽  
María G. Sánchez-Otero ◽  
Gerardo Valerio-Alfaro
Keyword(s):  
Aromatic Aldehyde ◽  
Candida Rugosa ◽  
Hydroxylamine Hydrochloride ◽  
Aromatic Aldehydes ◽  
Second Step ◽  
Acyl Donor ◽  
Porcine Pancreas ◽  
H Nmr ◽  
Novozyme 435 ◽  
Porcine Pancreas Lipase

The synthesis of aromatic aldehyde oxime esters (considered fragrances, antifungal and antimicrobial compounds) was achieved by two reactions which combine the advantage of green chemistry and biocatalysis. In the first step, the mechanochemical oxime synthesis by means of grindstone milling of six solid aromatic aldehydes and hydroxylamine hydrochloride in the presence of FlorisilR, as the best support, yielded the aromatic aldehyde oximes 1–6 with high purity and good yields. In the second step the lipase catalyzed acetylation reaction at 40°C for three days of those oximes with vinyl and isopropenyl acetates as acyl donor substrates and ethyl acetate as the solvent, yielded the aromatic aldehyde oxime esters. With Candida antarctica lipase (Novozyme 435), the conversions of oximes 1–6 into their esters were ≥ 99% according to the 1H NMR results and it was the best biocatalyst compared with others such as Candida rugosa (CRL), porcine pancreas lipase and the recombinant lipase LipMatCCR11 from the thermophilic strain Geobacillus thermoleovorans CCR11 cloned and expressed in Escherichia coli BL21 (DE3), all of which showed lower yields.

scholarly journals Application of natural kaolin as support for the immobilization of lipase from Candida rugosa as biocatalsyt for effective esterification

2005 ◽  
Vol 29 (2) ◽  
pp. 111-116 ◽  
Author(s):  
Mohd Basyaruddin Abdul Rahman ◽  
Safarini Md Tajudin ◽  
Mohd Zobir Hussein ◽  
Raja Nor Zaliha Raja Abdul Rahman ◽  
Abu Bakar Salleh ◽  
...  
Keyword(s):  
Candida Rugosa ◽  
Lipase From Candida Rugosa
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