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Volumn 13, Issue 6, 2002, Pages 537-542

The use of substrate engineering in biohydroxylation

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; AMINE; CARBON; CARBOXYLIC ACID DERIVATIVE; CYCLOALKANE DERIVATIVE; KETONE DERIVATIVE; LIPOXYGENASE; UNSPECIFIC MONOOXYGENASE; MIXED FUNCTION OXIDASE;

EID: 0036900863     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(02)00358-0     Document Type: Review
Times cited : (44)

References (17)
  • 1
    • 0003458664 scopus 로고    scopus 로고
    • K. Drauz, & H. Waldmann. Weinheim: Wiley-VCH
    • Drauz K., Waldmann H. Enzyme Catalysis in Organic Chemistry. 2002;Wiley-VCH, Weinheim.
    • (2002) Enzyme Catalysis in Organic Chemistry
  • 2
    • 0036525715 scopus 로고    scopus 로고
    • Oxidative biotransformations using oxygenases
    • Recent developments in biotransformations with oxygenases including nonactivated carbon, benzylic, allylic and aromatic hydroxylations are reviewed.
    • Li Z., van Beilen J., Duetz W.A., Schmid A., de Raadt A., Griengl H., Witholt B. Oxidative biotransformations using oxygenases. Curr Opin Chem Biol. 6:2002;136-144. Recent developments in biotransformations with oxygenases including nonactivated carbon, benzylic, allylic and aromatic hydroxylations are reviewed.
    • (2002) Curr Opin Chem Biol , vol.6 , pp. 136-144
    • Li, Z.1    Van Beilen, J.2    Duetz, W.A.3    Schmid, A.4    De Raadt, A.5    Griengl, H.6    Witholt, B.7
  • 3
    • 0033635584 scopus 로고    scopus 로고
    • Enzymatic hydroxylation reactions
    • A review dealing with various aspects of enzymatic hydroxylation reactions including new synthetic targets, new processes and mechanistic studies.
    • Holland H.L., Weber H.K. Enzymatic hydroxylation reactions. Curr Opin Biotechnol. 11:2000;547-553. A review dealing with various aspects of enzymatic hydroxylation reactions including new synthetic targets, new processes and mechanistic studies.
    • (2000) Curr Opin Biotechnol , vol.11 , pp. 547-553
    • Holland, H.L.1    Weber, H.K.2
  • 4
    • 0036525713 scopus 로고    scopus 로고
    • Protein engineering of oxygenases for biocatalysis
    • The scope and limitations of protein engineering in monooxygenase, dioxygenase and chloroperoxidase enzyme improvement are reviewed.
    • Cirino P.C., Arnold F.H. Protein engineering of oxygenases for biocatalysis. Curr Opin Chem Biol. 6:2002;130-135. The scope and limitations of protein engineering in monooxygenase, dioxygenase and chloroperoxidase enzyme improvement are reviewed.
    • (2002) Curr Opin Chem Biol , vol.6 , pp. 130-135
    • Cirino, P.C.1    Arnold, F.H.2
  • 5
    • 0033578652 scopus 로고    scopus 로고
    • The concept of docking/protecting groups in biohydroxylation
    • The docking/protecting group concept is introduced and brief examples of its application given, namely the hydroxylation of ketones, carboxylic acids, aldehydes and alcohols.
    • Braunegg G., de Raadt A., Feichtenhofer S., Griengl H., Kopper I., Lehmann A., Weber H.J. The concept of docking/protecting groups in biohydroxylation. Angew Chem Int Ed Engl. 38:1999;2763-2766. The docking/protecting group concept is introduced and brief examples of its application given, namely the hydroxylation of ketones, carboxylic acids, aldehydes and alcohols.
    • (1999) Angew Chem Int Ed Engl , vol.38 , pp. 2763-2766
    • Braunegg, G.1    De Raadt, A.2    Feichtenhofer, S.3    Griengl, H.4    Kopper, I.5    Lehmann, A.6    Weber, H.J.7
  • 6
    • 0035808421 scopus 로고    scopus 로고
    • The concept of docking and protecting groups in biohydroxylation
    • The docking/protecting group concept is covered in more detail for the hydroxylation of four different substance classes commonly used in preparative organic chemistry: ketones, alcohols, aldehydes and carboxylic acids.
    • de Raadt A., Griengl H., Weber H.J. The concept of docking and protecting groups in biohydroxylation. Chem Eur J. 7:2001;27-31. The docking/protecting group concept is covered in more detail for the hydroxylation of four different substance classes commonly used in preparative organic chemistry: ketones, alcohols, aldehydes and carboxylic acids.
    • (2001) Chem Eur J , vol.7 , pp. 27-31
    • De Raadt, A.1    Griengl, H.2    Weber, H.J.3
  • 9
    • 0035931531 scopus 로고    scopus 로고
    • Microbial hydroxylation of unsaturated, cyclic carboxylic acids protected as benzoxazoles
    • de Raadt A., Feichtenhofer S., Griengl H., Klingler M.F., Weber H. Microbial hydroxylation of unsaturated, cyclic carboxylic acids protected as benzoxazoles. J Mol Cat B: Enzym. 11:2001;361-366.
    • (2001) J Mol Cat B: Enzym , vol.11 , pp. 361-366
    • De Raadt, A.1    Feichtenhofer, S.2    Griengl, H.3    Klingler, M.F.4    Weber, H.5
  • 10
    • 0033674514 scopus 로고    scopus 로고
    • Chiral auxiliaries as docking/protecting groups in biohydroxylation: The hydroxylation of enantiopure spirooxazolidines derived from cyclopentanone using Beauveria bassiana ATCC 7159
    • de Raadt A, Fetz B, Griengl H, Klingler MF, Kopper I, Krenn B, Münzer DF, Ott RG, Plachota P, Weber HJ et al.: Chiral auxiliaries as docking/protecting groups in biohydroxylation: The hydroxylation of enantiopure spirooxazolidines derived from cyclopentanone using Beauveria bassiana ATCC 7159. Eur J Org Chem 2000, 3835-3847. For the first time chiral auxiliaries were used as docking/protecting groups in the biohydroxylation of cyclopentanone to improve product de and yield.
    • (2000) Eur J Org Chem , pp. 3835-3847
    • De Raadt, A.1    Fetz, B.2    Griengl, H.3    Klingler, M.F.4    Kopper, I.5    Krenn, B.6    Münzer, D.F.7    Ott, R.G.8    Plachota, P.9    Weber, H.J.10
  • 12
    • 0037012874 scopus 로고    scopus 로고
    • Selectivity of biohydroxylation with Beauveria bassiana of trans-2-fluorocycloalkyl N-phenylcarbamates
    • Haufe G., Wölker D., Fröhlich R. Selectivity of biohydroxylation with Beauveria bassiana of trans-2-fluorocycloalkyl N-phenylcarbamates. J Org Chem. 67:2002;3022-3028.
    • (2002) J Org Chem , vol.67 , pp. 3022-3028
    • Haufe, G.1    Wölker, D.2    Fröhlich, R.3
  • 13
    • 0035861695 scopus 로고    scopus 로고
    • Preparation of (R)- and (S)-N-protected 3-hydroxypyrrolidines by hydroxylation with Sphingomonas sp. HXN-200, a highly active, regio- and stereoselective, and easy to handle biocatalyst
    • Resting as well as frozen/thawed Sphingomonas sp. cells were used to regio- and stereoselectively hydroxylate N-substituted pyrrolidine derivatives. The configuration of the hydroxylated product could be determined by the choice of N-substituent.
    • Li Z., Feiten H.J., Chang D., Duetz W.A., van Beilen J.B., Witholt B. Preparation of (R)- and (S)-N-protected 3-hydroxypyrrolidines by hydroxylation with Sphingomonas sp. HXN-200, a highly active, regio- and stereoselective, and easy to handle biocatalyst. J Org Chem. 66:2001;8424-8430. Resting as well as frozen/thawed Sphingomonas sp. cells were used to regio- and stereoselectively hydroxylate N-substituted pyrrolidine derivatives. The configuration of the hydroxylated product could be determined by the choice of N-substituent.
    • (2001) J Org Chem , vol.66 , pp. 8424-8430
    • Li, Z.1    Feiten, H.J.2    Chang, D.3    Duetz, W.A.4    Van Beilen, J.B.5    Witholt, B.6
  • 14
    • 0037198750 scopus 로고    scopus 로고
    • Practical syntheses of N-substituted 3-hydroxyazetidines and 4-hydroxypiperidines by hydroxylation with Sphingomonas sp. HXN-200
    • Frozenthawed Sphingomonas sp. HXN-200 cells were used to regioselectively hydroxylate N-substituted azetidine and piperidine derivatives in high yields. For the first time, rehydrated lyophilized cells could also be used.
    • Chang D., Feiten H.J., Engesser K.H., van Beilen J.B., Witholt B., Li Z. Practical syntheses of N-substituted 3-hydroxyazetidines and 4-hydroxypiperidines by hydroxylation with Sphingomonas sp. HXN-200. Org Lett. 4:2002;1859-1862. Frozenthawed Sphingomonas sp. HXN-200 cells were used to regioselectively hydroxylate N-substituted azetidine and piperidine derivatives in high yields. For the first time, rehydrated lyophilized cells could also be used.
    • (2002) Org Lett , vol.4 , pp. 1859-1862
    • Chang, D.1    Feiten, H.J.2    Engesser, K.H.3    Van Beilen, J.B.4    Witholt, B.5    Li, Z.6
  • 15
    • 0034736384 scopus 로고    scopus 로고
    • Preparation of (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones by regio- and stereoselective hydroxylation with Sphingomonas sp. HXN-200
    • Chang D., Witholt B., Li Z. Preparation of (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones by regio- and stereoselective hydroxylation with Sphingomonas sp. HXN-200. Org Lett. 2:2000;3949-3952.
    • (2000) Org Lett , vol.2 , pp. 3949-3952
    • Chang, D.1    Witholt, B.2    Li, Z.3
  • 16
    • 0035968393 scopus 로고    scopus 로고
    • Enzymatic asymmetric hydroxylation of unnatural substrates with soybean lipoxygenase
    • With the aid of substrate engineering, unnatural substrates could be hydroxylated employing soybean lipoxygenase and a chemical reduction.
    • Yadav J.S., Nanda S., Bhaskar Rao A. Enzymatic asymmetric hydroxylation of unnatural substrates with soybean lipoxygenase. Tetrahedron Asymmetry. 12:2001;2129-2135. With the aid of substrate engineering, unnatural substrates could be hydroxylated employing soybean lipoxygenase and a chemical reduction.
    • (2001) Tetrahedron Asymmetry , vol.12 , pp. 2129-2135
    • Yadav, J.S.1    Nanda, S.2    Bhaskar Rao, A.3
  • 17
    • 0034987387 scopus 로고    scopus 로고
    • Soybean lipoxygenase and horseradish peroxidase catalysed asymmetric oxidation-reduction sequence for the synthesis of chiral (Z,E) diene-diols
    • Yadav JS, Nanda S, Bhaskar Rao A: Soybean lipoxygenase and horseradish peroxidase catalysed asymmetric oxidation-reduction sequence for the synthesis of chiral (Z,E) diene-diols. Synlett 2001, 787-788.
    • (2001) Synlett , pp. 787-788
    • Yadav, J.S.1    Nanda, S.2    Bhaskar Rao, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.