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Journal

2014 | 1 | 1 |

Article title

Biocatalytic deracemization: An efficient one-pot
synthesis of (R)-α-methyl-4-pyridinemethanol
using whole cells of Candida parapsilosis

Content

Title variants

Languages of publication

EN

Abstracts

EN

Publisher

Journal

Year

Volume

1

Issue

1

Physical description

Dates

online
10 - 9 - 2015
received
15 - 5 - 2015
accepted
20 - 7 - 2015

Contributors

  • Department of Pharmaceutical
    Technology, National Institute of Pharmaceutical Education and
    Research, Sector-67, S. A. S. Nagar-160062, Punjab, India
author
  • Department of Pharmaceutical
    Technology, National Institute of Pharmaceutical Education and
    Research, Sector-67, S. A. S. Nagar-160062, Punjab, India
  • Department of Pharmaceutical
    Technology, National Institute of Pharmaceutical Education and
    Research, Sector-67, S. A. S. Nagar-160062, Punjab, India

References

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  • [2] Kaneoya M., Uchida M., Yoshida N., U.S. Patent No. 4,971,909,1990.
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  • [4] Collomb P., Von Zelewsky A., Synthesis of new chiral catalysts,pyridyl-and bipyridyl-alcohols, for the enantioselectiveaddition of diethylzinc to benzaldehyde, Tetrahedron:Asymmetry, 1998, 9, 3911-3917.[Crossref]
  • [5] Okano K., Murata K., Ikariya T., Stereoselective synthesisof optically active pyridyl alcohols via asymmetric transferhydrogenation of pyridyl ketones, Tetrahedron Lett., 2000, 41,9277-9280.[Crossref]
  • [6] Brown E., Penfornis A., Bayma J., Touet J., Asymmetricreductions of ketones using lithium aluminium hydridemodified with N, N-dialkyl derivatives of (R)-(−)-2-aminobutan-1-ol, Tetrahedron: Asymmetry, 1991, 2, 339-342.[Crossref]
  • [7] Lee J.H., Kim N., Kim M.J., Park J., Substituent effect on catalyticactivities of [{η5- Ar4C4COC(=O)Ar}Ru(CO)2Cl] in racemizationand DKR of secondary alcohols, ChemCatChem, 2011, 3,354-359.
  • [8] Seemayer R., Schneider M.P., Preparation of optically purepyridyl-1-ethanols, Tetrahedron: Asymmetry, 1992, 3, 827-830.[Crossref]
  • [9] Uenishi J.I., Hiraoka T., Hata S., Nishiwaki K., Yonemitsu O.,Nakamura K., Tsukube H., Chiral pyridines: optical resolutionof 1-(2-pyridyl)-and 1-[6-(2, 2’-bipyridyl)] ethanols by lipasecatalyzedenantioselective acetylation, J. Org. Chem., 1998, 63,2481-2487.[Crossref]
  • [10] Hatzakis N.S., Smonou I., Asymmetric transesterificationof secondary alcohols catalyzed by feruloyl esterase fromHumicola insolens, Bioorg. Chem., 2005, 33, 325-337.[Crossref]
  • [11] Laumen K., Schneider M.P., A highly selective ester hydrolasefrom Pseudomonas sp. for the enzymatic preparation ofenantiomerically pure secondary alcohols; chiral auxiliaries inorganic synthesis, Chem Commun., 1988, 9, 598-600.[Crossref]
  • [12] Gruber C.C., Lavandera I., Faber K., Kroutil W., From a racemateto a single enantiomer: deracemization by stereoinversion,Adv. Synth. Catal., 2006, 348, 1789-1805.
  • [13] Voss C.V., Gruber C.C., Kroutil W., Deracemization of secondaryalcohols through a concurrent tandem biocatalytic oxidationand reduction, Angew. Chem., Int. Ed., 2008, 47, 741-745.[Crossref][WoS]
  • [14] Nie Y., Xu Y., Mu X.Q., Highly enantioselective conversion ofracemic 1-phenyl-1, 2-ethanediol by stereoinversion involvinga novel cofactor-dependent oxidoreduction system of Candidaparapsilosis CCTCC M203011, Org. Process Res. Dev., 2004, 8,246-251.[Crossref]
  • [15] Nakamura K., Fujii M., Ida Y., Stereoinversion of arylethanolsby Geotrichum candidum, Tetrahedron: Asymmetry, 2001, 12,3147-3153.[Crossref]
  • [16] Xie S.X., Ogawa J., Shimizu S., Production of (R)-3-pentyn-2-olthrough stereoinversion of racemic 3-pentyn-2-ol by Nocardiafusca AKU 2123. Appl. Microbiol. Biotechnol. 1999, 52, 327-331.[Crossref]
  • [17] Gamenara D., Domínguez de María P., Candida spp. redoxmachineries: An ample biocatalytic platform for practicalapplications and academic insights. Biotechnol. Adv., 2009,27, 278-285.[WoS][Crossref]
  • [18] Nestl B.M., Voss C.V., Bodlenner A., Ellmer-Schaumberger U.,Kroutil W., Faber K., Biocatalytic racemization of sec-alcoholsand α-hydroxyketones using lyophilized microbial cells, Appl.Microbiol. Biotechnol., 2007, 76, 1001-1008.[Crossref][WoS]
  • [19] Baskar B., Pandian N.G., Priya K., Chadha A., Deracemisationof aryl substituted α-hydroxy esters using Candida parapsilosisATCC 7330: effect of substrate structure and mechanism,Tetrahedron, 2005, 61, 12296-12306.
  • [20] Banoth L., Banerjee U.C., New Chemical and Chemo-enzymaticsynthesis of (RS)-, (R)-, and (S)-Esmolol, Arabian J. Chem., (inpress), DOI:10.1016/j.arabjc.2014.03.011.[Crossref]
  • [21] Padhi S.K., Chadha A., Deracemisation of aromatic β-hydroxyesters using immobilized whole cells of Candida parapsilosisATCC 7330 and determination of absolute configuration by 1HNMR, Tetrahedron: Asymmetry, 2005, 16, 2790-2798.
  • [22] Titu D., Chadha A., Enantiomerically pure allylic alcohols:preparation by Candida parapsilosis ATCC 7330 mediatedderacemisation, Tetrahedron: Asymmetry, 2008, 19, 1698-1701.[WoS][Crossref]
  • [23] Saravanan T., Chadha A., Biocatalytic deracemization ofalkyl-2-hydroxy-4-arylbut-3-ynoates using whole cells ofCandida parapsilosis ATCC 7330, Tetrahedron: Asymmetry,2010, 21, 2973-2980.[WoS][Crossref]
  • [24] Guezane S.L., Djerourou A., Esterification and etherificationof steroid and terpene under Mitsunobu conditions, Arabian J.Chem., (in press), DOI: 10.1016/j.arabjc.2011.09.008.[Crossref]
  • [25] Salihu A., Alam M.Z., Karim M.I.A., Salleh H.M., Esterificationfor butyl butyrate formation using Candida cylindracea lipaseproduced from palm oil mill effluent supplemented medium,Arabian J. Chem., (in press), DOI: 10.1016/j.arabjc.2013.08.012.[WoS][Crossref]
  • [26] Orrenius C., Mattson A., Norin T., Ohrner N., Hult K.,Preparation of 1-pyridinyl-ethanols of high enantiomericpurity by lipase catalysed transesterifications, Tetrahedron:Asymmetry, 1994, 5, 1363-1366.[Crossref]
  • [27] Soni P., Kaur G., Chakraborti A., Banerjee U.C., Candidaviswanathii as a novel biocatalyst for stereoselective reductionof heteroaryl methyl ketones: A highly efficient enantioselectivesynthesis of (S)-α-(3-pyridyl)ethanol. Tetrahedron:Asymmetry, 2005, 16, 2425-2428.[Crossref]
  • [28] Päiviö M., Mavrynsky D., Leino R., Kanerva, L.T., Dynamickinetic resolution of a wide range of secondary alcohols:Cooperation of dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B, Eur. J. Org. Chem., 2011,1452-1457.[Crossref][WoS]
  • [29] Machado L.L., Gonzalo G.D., Lemos T.L.G., Mattosa M.C.D.,Oliveira, M.C.F., Fernández V.G., Gotor V., Enantioselectiveacetylation of racemic alcohols by Manihot esculenta andPassiflora edulis preparations, J. Mol. Catal. B: Enzymatic,2009, 60, 157-162.[WoS][Crossref]
  • [30] Singh A., Chisti Y., Banerjee U.C., Stereoselective biocatalytichydride transfer to substituted acetophenones by the yeastMetschnikowia koreensis, Process Biochem., 2012, 47,2398-2404.[Crossref][WoS]
  • [31] Kansal H., Banerjee U.C., Enhancing the biocatalytic potentialof carbonyl reductase of Candida viswanathii using aqueousorganicsolvent system. Bioresour. Technol., 2009, 100,1041-1047.[Crossref][WoS]
  • [32] Stella S., Chadha A., Biocatalytic reduction of α-keto amides to(R)-α-hydroxy amides using Candida parapsilosis ATCC 7330,Catal. Today, 2012, 198, 345-352.[WoS]
  • [33] Zhu D., Malik H.T., Hua L., Asymmetric ketone reduction bya hyperthermophilic alcohol dehydrogenase. The substratespecificity, enantioselectivity and tolerance of organic solvents,Tetrahedron: Asymmetry, 2006, 17, 3010-3014.[Crossref]
  • [34] Laane C., Boeren S., Vos K., Veeger C. Rules for optimization ofbiocatalysis in organic solvents, Biotechnol. Bioeng., 1987, 30,81-87.[Crossref]
  • [35] Nakamura K., Inoue Y., Ohno A., Improvement of enantioselectivityof microbial reduction by using organic solvent redoxcoupler system, Tetrahedron Lett., 1995, 36, 265-266[Crossref]

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_1515_boca-2015-0004
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