70267-24-2

Upstream product

• 84277-81-6 L-2-aminodecanoic acid 
• 84276-16-4 D-2-aminodecanoic acid 
• 5393-81-7 DL-2-hydroxydecanoic acid 
• 5440-55-1 acetylamino-octyl-malonic acid diethyl ester 
• 84209-81-4 rac-2-(chloroacetylamino)decanoic acid 
• 111-83-1 1-bromo-octane 
• 17702-88-4 rac-2-aminodecanoic acid 
• 334-48-5 1-decanoic acid 

Downstream Products

• 381718-96-3 (R)-1-O-Benzyl-1,2-decandiol 

Relevant academic research and scientific papers

Enantioselective α hydroxylation of carboxylic acids with molecular oxygen catalyzed by the α oxidation enzyme system of young pea leaves (Pisum sativum): A substrate selectivity study

The substrate selectivity of the α oxidation of carboxylic acids 1 by crude homogenate of young pea leaves was investigated. Saturated fatty acids with 7 to 16 carbon atoms and oleic acid were transformed to the enantiomerically pure (R)-2-hydroxy acids 2 in the presence of molecular oxygen.

Light-Driven Kinetic Resolution of α-Functionalized Carboxylic Acids Enabled by an Engineered Fatty Acid Photodecarboxylase

Chiral α-functionalized carboxylic acids are valuable precursors for a variety of medicines and natural products. Herein, we described an engineered fatty acid photodecarboxylase (CvFAP)-catalyzed kinetic resolution of α-amino acids and α-hydroxy acids, which provides the unreacted R-configured substrates with high yields and excellent stereoselectivity (ee up to 99 %). This efficient light-driven process requires neither NADPH recycling nor prior preparation of esters, which were required in previous biocatalytic approaches. The structure-guided engineering strategy is based on the scanning of large amino acids at hotspots to narrow the substrate binding tunnel. To the best of our knowledge, this is the first example of asymmetric catalysis by an engineered CvFAP.

Synthesis of optically active α-hydroxy acids by kinetic resolution through lipase-catalyzed enantioselective acetylation

The lipase-catalyzed acetylation of a broad spectrum of racemic 2-hydroxy acids 1 to their 2-acetoxy acids 2 was shown to proceed with high enantioselectivity. Thus, the microbial lipases, in particular from Candida antarctica and Burkholderia species, are convenient biocatalysts for the synthesis of optically active 2-hydroxy acids in excellent enantioselectivity (ee values up to 99%). The absolute configurations of the 2-hydroxy acids 1 were assigned by comparison of the gas-chromatographic data with that of literature-known reference compounds, or by means of the exciton-coupled circular dichroism method (ECCD) on their bichromophoric 2-naphthoate 9-anthrylmethyl derivatives 3. These results establish that (S)-2-hydroxy acids 1 were preferentially acetylated by microbial lipases.

Enzymatic Resolution of Chiral 2-Hydroxy Carboxylic Acids by Enantioselective Oxidation with Molecular Oxygen Catalyzed by the Glycolate Oxidase from Spinach (Spinacia oleracea)

The enzymatic oxidation of a variety of saturated and unsaturated aliphatic derivatives of racemic 2-hydroxy acids 1 to their 2-oxo acids 2 with molecular oxygen catalyzed by the glycolate oxidase from spinach (Spinacia oleracea) was shown to proceed highly enantioselectively.Thus, the glycolate oxidase-catalyzed kinetic resolution provides a convenient biocatalytic method for the preparation of enantiomerically pure (R)-2-hydroxy acids.The absolute configuration of the (R)-2-hydroxy acid 1b assigned by comparison of the measured optical rotation value with that of the literature data and by application of the exciton-coupled circular dichroism method (ECCD) on its bichromophoric 2-naphthoate 9-methylanthryl derivative 3b.These results establish the ECCD method as a convenient microscale chirooptic tool for the configurational assignment of 2-hydroxy acids.

Synthesis of intermediates in the preparation of ACAT inhibitors

This invention relates to novel processes for synthesizing intermediates in the preparation of N-aryl and N-heteroarylamide inhibitors of the enzyme acyl coenzyme A: cholesterol acyltransferase (ACAT), and to novel intermediates used in such processes.

Tailoring Lipase Specificity by Solvent and Substrate Chemistries

An acyl binding structural model has been developed to explain the observed catalytic efficiencies and enantioselectivities of Candida rugosa lipase-catalyzed (trans)esterification reactions involving 2-hydroxy acids and vinyl esters, respectively, and acylation reactions involving both cyclic and acyclic alcohols.A clear minimum was observed for (trans)esterification of six-carbon acyl moieties.Moreover, the stereoselectivity of 2-hydroxy acid esterification in a number of hydrophilic and hydrophobic solvents was dependent on the acyl chain length: S-isomers of 2-hydroxy acids were acylated for acyl chain lengths of six or fewer, whereas the R-isomers were preferentially esterified for acyl chain lengths of eight or more.These results suggest that CRL contains both large and small acyl binding regions or pockets with high catalysis observed for proper fitting substrates into either pocket.CRL is also highly selective and reactive on secondary cyclic alcohols.In particular, the R isomers of menthol and sec-phenethanol are acylated efficiently by straight-chain vinyl esters.The catalytic efficiency of acylation (i.e., Vmax/Km for the secondary alcohol) is strongly dependent on the acyl chain length.Once again, a clear minimum is observed with vinyl caproate (C6) as acyl donor.This phenomenon may reflect the greater degree of steric hinderance in the acyl enzyme intermediate caused by the caproate group.A mechanistic and thermodynamic rationale was proposed for the effects of solvent and substrate chemistries on CRL catalysis on organic solvents.

An Efficient Synthesis of (S)-2-Hexylthiodecanoic Acid

A short synthesis of (S)-2-hexylthiodecanoic acid from racemic 2-hydroxydecanoic acid is described.This material is useful as a sidechain for ACAT inhibitors.

Synthesis of Both the Enantiomers of 4-Dodecanolide, a Defensive Secretion of Rove Beetles

The enantiomers of 4-dodecanolide, a defensive secretion of rove beetles, were synthesized from (S)- and (R)-2-aminodecanoic acid obtained by the enzymic resolution of the corresponding chloroacetyl derivative.