Protein Information

Name lipase
Synonyms HGL; HPL; HGL; Human giant larvae homolog; LGL 2; LGL2; LLGL 2; LLGL2…

Compound Information

Name sulfoxide
CAS 5-[2-(octylsulfinyl)propyl]-1,3-benzodioxole

Reference List

PubMed Abstract RScore(About this table)
18543116 Costas L, Bosio VE, Pandey A, Castro GR: Effects of organic solvents on immobilized lipase in pectin microspheres. Appl Biochem Biotechnol. 2008 Dec;151(2-3):578-86. Epub 2008 Jun 10.

6(0,0,0,6) Details
19731302 Kawata T, Ogino H: Enhancement of the organic solvent-stability of the LST-03 lipase by directed evolution. Biotechnol Prog. 2009 Nov-Dec;25(6):1605-11.

6(0,0,0,6) Details
19361213 Ge J, Lu D, Wang J, Liu Z: Lipase nanogel catalyzed transesterification in anhydrous dimethyl sulfoxide. Biomacromolecules. 2009 Jun 8;10(6):1612-8.

5(0,0,0,5) Details
18571801 Liu Y, Wang F, Tan T: Cyclic resolution of racemic ibuprofen via coupled efficient lipase and acid-base catalysis. Chirality. 2009 Mar;21(3):349-53.

4(0,0,0,4) Details
18074337 Ammazzalorso A, Amoroso R, Bettoni G, De Filippis B, Fantacuzzi M, Giampietro L, Maccallini C, Tricca ML: Candida rugosa lipase-catalysed kinetic resolution of 2-substituted-aryloxyacetic esters with dimethylsulfoxide and isopropanol as additives. Chirality. 2008 Feb;20(2):115-8.

3(0,0,0,3) Details
17616461 Singh M, Singh S, Singh RS, Chisti Y, Banerjee UC: Transesterification of primary and secondary alcohols using Pseudomonas aeruginosa lipase. Bioresour Technol. 2008 May;99(7):2116-20. Epub 2007 Jul 9.

2(0,0,0,2) Details
19072546 Kato M, Toshima K, Matsumura S: Direct enzymatic synthesis of a polyester with free pendant mercapto groups. Biomacromolecules. 2009 Feb 9;10(2):366-73.


An aliphatic polyester with free pendant mercapto groups was prepared by direct lipase-catalyzed polycondensation of hexane-1,6-diol and dimethyl 2-mercaptosuccinate.
2(0,0,0,2) Details
19428729 Invernizzi G, Casiraghi L, Grandori R, Lotti M: Deactivation and unfolding are uncoupled in a bacterial lipase exposed to heat, low pH and organic solvents. J Biotechnol. 2009 Apr 20;141(1-2):42-6. Epub 2009 Mar 16.

2(0,0,0,2) Details
20099862 Patterson LD, Miller MJ: Enzymatic deprotection of the cephalosporin 3'-acetoxy group using Candida antarctica lipase B. J Org Chem. 2010 Feb 19;75(4):1289-92.

Although this transformation is difficult to carry out using chemical methods, the enzymatic deacetylation has been successful on gram scale, when the cephalosporin is protected as either the benzhydryl or tert-butyl esters and on the corresponding sulfoxide and sulfone of the tert-butyl ester.
2(0,0,0,2) Details
18452392 Wang Y, Chanda P, Jones PG, Kennedy JD: A fluorescence-based assay for monoacylglycerol lipase compatible with inhibitor screening. Assay Drug Dev Technol. 2008 Jun;6(3):387-93.

2(0,0,0,2) Details
20352971 Zheng S, Ren C, Han S, Lin Y: [Synthesis of glucose laurate monoester catalyzed by Candida antarctica lipase B-displaying Pichia pastoris whole-cells]. Sheng Wu Gong Cheng Xue Bao. 2009 Dec;25(12):1933-9.

Then we optimized the process from various aspects, such as solvent composition, ratio of dmethyl sulfoxide to 2-Methyl-2-butanol (V/V), catalyst dosage, substrate concentration, water activity and temperature.
2(0,0,0,2) Details
17511027 Seo SW, Jung WS, Piao TG, Hong SH, Yun KJ, Park RK, Shin MK, Song HJ, Park SJ: Selective cyclooxygenase-2 inhibitor ameliorates cholecystokinin-octapeptide-induced acute pancreatitis in rats. World J Gastroenterol. 2007 Apr 28;13(16):2298-304.


RESULTS: SC-236 improved the severity of CCK-octapeptide-induced AP as measured by laboratory criteria [the pancreatic weight/body weight (p.w/b.w) ratio, the level of serum amylase and lipase].
1(0,0,0,1) Details
20090969 O'Byrne A, Murray C, Keegan D, Palacio C, Evans P, Morgan BS: The thio-adduct facilitated, enzymatic kinetic resolution of 4-hydroxycyclopentenone and 4-hydroxycyclohexenone. Org Biomol Chem. 2010 Feb 7;8(3):539-45. Epub 2009 Nov 30.

In both cases, subsequent treatment with vinyl acetate, in the presence of a lipase enabled enantiomer resolution.
Then using the same starting material a 6-step sequence, featuring a diastereoselective NaBH4 reduction and a Cope-type sulfoxide elimination, gave (-)-19.
1(0,0,0,1) Details