Regioselective acylation of several polyhydroxylated natural compounds by Candida antarctica lipase B

Biocatalysis and Biotransformation

Volumn 23, Issue 2, 2005, Pages 109-116

  Teng, Rong Wei ^a   Bui, Thi Kim Anh ^b   McManus, David ^c   Armstrong, David ^c   Mau, Shaio Lim ^a   Bacic, Antony ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b HO CHI MINH CITY UNIVERSITY OF TECHNOLOGY   (Viet Nam)

^c Albright and Wilson Australia Ltd   (Australia)

Author keywords

Acylation; Asperulosidic acid; Candida antarctica Lipase B; Deacetyl asperulosidic acid; Puerarin; Resveratrol

Indexed keywords

ENZYMES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS;

ASPERULOSIDIC ACID; POLYHYDROXYLATED NATURAL COMPOUNDS; REGIOSELECTIVE ACYLATION; VINYL DECANOATE;

ORGANIC ACIDS;

ASPERULOSIDIC ACID; DECANOIC ACID DERIVATIVE; LIPASE B; MORINDA CITRIFOLIA EXTRACT; PUERARIN; RESVERATROL; UNCLASSIFIED DRUG; VINYL ACETATE; VINYL DERIVATIVE;

ACETYLATION; ACYLATION; ARTICLE; CANDIDA ANTARCTICA; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; HYDROXYLATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTITATIVE ANALYSIS;

CANDIDA ANTARCTICA;

EID: 21844434923     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.1080/1024220500132508     Document Type: Article

References (31)

1. Brunet C, Zarevucka M, Zdenek W, Legoy MD. 2002. Total enzymatic resolution of racemic 2-(4-methoxylbenzyl)-1-cyclohexanols and 2-(4-methoxylbenzyl)-1-cyclopentanols. Enzyme Microb Techno 31:609-614.
2. Cheng G, Bai Y, Zhao Y, Tao J, Lin Y, Tu G, Ma L, Liao N, Xu X. 2000. Flavonoids from Ziziphus jujuba Mill var. spinosa. Tetrahedron 56:8915-8920.
3. Danieli B, Bertario A, Carrea G, Redigolo B, Secundo F, Riva S. 1993. Chemo-enzymatic synthesis of 6″-O-(3-arylprop-2-enoyl) dericatives of the flavonol glucoside isoquercitrin. Helv Chim Acta 76:2981-2991.
4. Danieli B, Luisetti M, Steurer S, michelitsch A, Likussar W, Riva S, Reiner J, Schubert-Zsilavecz M. 1999. Application of lipase-catalyzed regioselective esterification in the preparation of digitonin derivatives. J Nat Prod 62:670-673.
5. Davis BG, Boyer V. 2001. Biocatalysts and enzymes in organic synthesis. Nat Prod Rep 18:618-640.
6. Enaud E, Humeau C, Piffaut B, Girardin M. 2004. Enzymatic synthesis of new aromatic esters of phloridzin. J Mol Catal B 27:1-6.
7. Gupta S, Mukhtar H. 2002. Chemoprevention of skin cancer: current status and future prospects. Cancer Metast Rev 21:363-380.
8. Jacobsen EE, Hellemond E V, Riise Moen A, Vazquez Prado L C, Anthonsen T. 2003. Enhanced selectivity in Novozyme 435 catalyzed kinetic resolution of secondary alcohols and butanoates caused by the (R)-alcohols. Tetrahedron Lett 44:8453-8455.
9. Jaeger KE. 2004. Protein technologies and commercial enzymes white is the hype-biocatalysts on the move. Curr Opin Biotech 15:269-271.
10. Khmelnitsky YL, Budde C, Arnold JM, Usyatinsky A, Clark DS, Dordick JS. 1997. Synthesis of water-soluble paclitaxel derivatives by enzymatic acylation. J Am Chem Soc 119:11554-11555.
11. Kontogianni A, Skouridou V, Sereti V, Stamatis H, Kolisis FN. 2002. Lipase-catalyzed esterification of rutin and naringin with fatty acids of medium carbon chain. J Mol Catal B 765:1-4.
12. Lai XL, Tang B. 1989. Recent advances in the experimental study and clinical application of Pueraria lobata (Willd) Ohwi. Zhongguo Zhong Yao Za Zhi 14:308-311.
13. Liu G, Bode A, Ma WY, Sang S, Ho CT, Dong Z. 2001. Two novel glycosides from the fruits of Morina citrifolia (Noni) inhibit AP-1 transactivation and cell transformation in the mouse epidermal JB6 cell line. Cancer Res 61:5749-5756.
14. Nicolosi G, Spatafora C, Tringali C. 2002. Chemo-enzymatic preparation of resveratrol derivatives. J Mol Catal B 16:223-229.
15. Oosterom MWV, Rantwijk FV, Sheldon RA. 1996. Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica lipase. Biotechnol Bioeng 49:328-333.
16. Pedersen NR, Wimmer R, Emmersen J, Degn P, Pedersen LH. 2002. Effect of fatty acid chain length on initial reaction rates and regioselectivity of lipase-catalysed esterification of disaccharides. Carbohydr Res 337:1179-1184.
17. 13C NMR spectroscopy of naturally occurring iridoid glucosides and their acylated derivatives. Tetrahedron 36:2317-2326.
18. Romero-Pérez AI, Lamuela-Raventós RM, Andrés-lacueva A, Torre-Boronat MCDL. 2001. Methods for quantitative extraction of resveratrol and piceid isomers in grape berry skins, effect of powdery mildew on stilbene content. J Agric Food Chem 49:210-215.
19. Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B. 2001. Industrial biocatalysis today and tomorrow. Nature 409:258-268.
20. Schoemaker HE, Mink D, Wubbolts MG. 2003. Dispelling the myths-biocatalysis in industrial synthesis. Science 229:1694-1697.
21. Skupinska KA, McEzchern EJ, Baird IR, Skerli RT, Bridger GJ. 2003. Enzymatic resolution of bicyclic 1-Heteroarylamines using Candida antarctica lipase B. J Org Chem 68:3546-3551.
22. Tasdemir D, Scapozza L, Zerve O, Linden A, Calis I, Sticher O. 1999. Iridoid glycosides of Leonurus persicus. J Nat Prod 62:811-816.
23. Teng R, Ang C, McManus D, Armstrong D, Mau S, Bacic A. 2004. Regioselective acylation of ginsenosides by Novozyme 435. Tetrahedron Lett 44:5661-5664.
24. Teng R, Ang C, McManus D, Armstrong D, Mau S, Bacic A. 2004. Regioselective acylation of ginsenosides by Novozyme 435 to generate molecular diversity. Helv Chim Acta 87:1860-1872.
25. Teng R, Wang D, Wu Y, Lu Y, Zhen QT, Yang C. 2005. NMR assignments and single crystal X-ray diffraction analysis of Deoxyloganic Acid. Magn Reson Chem 43:92-96.
26. Uppenberg J, Hansen MT, Patkar S, Jones TA. 1994. The sequence, crystal structure determination and refinement of two crystal forms lipase B from Candida antarctica. Structure 2:293-308.
27. Uppenberg J, Oehrner N, Norin M, Hult K, Kleywegt GJ, Patkar S, Waagen V, Anthonsen T, Jones TA. 1995. Crystallographic and molecular-modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols. Biochemistry 34:16838-16851.
28. Wang M, Kikuzaki H, Csiszar K, Boyd CD, Maunakea A, Fong SFT, Ghai G, Rosen RT, Nakatani N, Ho CT. 1999. Novel trisaccharide fatty acid ester identified from the fruits of Morinda citrifolia (Noni). J Agric Food Chem 47:4880-4882.
29. Yang R, Li N, Bo X, Chiou GCY, Min Z. 1999. Preparation and bioactivity of puerarin derivatives. Zhongguo Yaoke Daxue Xuebao 30:81-85.
30. Yu B, Xing G, Hui Y, Han X. 2001. Lipase-catalyzed regioselective acylation of diosgenyl saponins. Tetrahedron Lett 42:5513-5515.
31. Zhu JH, Wang XX, Chen JZ, Shang YP, Zhu JH, Guo XG, Sun J. 2004. Effects of puerarin on number and activity of endothelial progenitor cells from peripheral blood. Acta Pharmacol Sin 25:1045-1051.