Lipase catalysed acylation of hydroxylamine and hydrazine derivatives

被引：15

作者：

Hacking, MAPJ ^{[1
]}

van Rantwijk, F ^{[1
]}

Sheldon, RA ^{[1
]}

机构：

[1] Delft Univ Technol, Organ Chem & Catalysis Lab, NL-2628 BL Delft, Netherlands

来源：

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 2001年 / 11卷 / 4-6期

关键词：

lipase; acyl transfer; hydroxylamine; hydrazine; ibuprofen;

D O I：

10.1016/S1381-1177(00)00144-2

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The lipase catalysed acylation of hydroxylamine-and hydrazine as well as their derivatives by octanoic acid is very efficient. Cross-linked crystals of Candida rugosa Lipase (ChiroCLEC-CR) mediated the conversion of racemic ibuprofen into (S)-ibuproxam. A number of lipases also catalysed the condensation of hydrazine with an excess of octanoic acid giving N,N'-dioctanoylhydrazine. The hydrazide of 2-(4-isobutylphenyl)propanoic acid (ibuprofen), prepared by non-enzymatic reaction of ibuprofen methyl ester with hydrazine, acted as nucleophile towards several lipases that do not accept ibuprofen derivatives as acyl donor. (C) 2001 Elsevier Science B.V. All rights reserved.

引用

页码：315 / 321

页数：7

共 14 条

[1]

ASTORGA C, 1993, SYNTHESIS-STUTTGART, P287

[2] LIPASE-CATALYZED TRANSFORMATIONS WITH UNNATURAL ACYL ACCEPTERS [J].

DEZOETE, MC ;

VANRANTWIJK, F ;

SHELDON, RA .

CATALYSIS TODAY, 1994, 22 (03) :563-590

[3] Synthesis of primary amides by lipase-catalyzed amidation of carboxylic acids with ammonium salts in an organic solvent [J].

Litjens, MJJ ;

Straathof, AJJ ;

Jongejan, JA ;

Heijnen, JJ .

CHEMICAL COMMUNICATIONS, 1999, (13) :1255-1256

[4] Enzymatic synthesis of glycamide surfactants by amidification reaction [J].

Maugard, T ;

RemaudSimeon, M ;

Petre, D ;

Monsan, P .

TETRAHEDRON, 1997, 53 (14) :5185-5194

[5] Kinetic study of chemoselective acylation of amino-alditol by immobilized lipase in organic solvent: effect of substrate ionization [J].

Maugard, T ;

Remaud-Simeon, M ;

Monsan, P .

BIOCHIMICA ET BIOPHYSICA ACTA-PROTEIN STRUCTURE AND MOLECULAR ENZYMOLOGY, 1998, 1387 (1-2) :177-183

[6] Lipase-catalysed production of N-oleoyl-taurine sodium salt in non-aqueous medium [J].

Maugard, T ;

RemaudSimeon, M ;

Petre, D ;

Monsan, P .

BIOTECHNOLOGY LETTERS, 1997, 19 (08) :751-753

[7]

PEDERSEN S, 1990, Patent No. 9015868

[8] SYNTHESIS OF FATTY HYDROXAMIC ACIDS CATALYZED BY THE LIPASE OF MUCOR-MIEHEI [J].

SERVAT, F ;

MONTET, D ;

PINA, M ;

GALZY, P ;

ARNAUD, A ;

LEDON, H ;

MARCOU, L ;

GRAILLE, J .

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1990, 67 (10) :646-649

[9]

SERVAT F, 1990, TENSIDE SURFACT DET, V27, P298

[10] LIPASE-CATALYZED SYNTHESES OF N-OCTYL-ALKYLAMIDES IN ORGANIC MEDIA [J].

TUCCIO, B ;

FERRE, E ;

COMEAU, L .

TETRAHEDRON LETTERS, 1991, 32 (24) :2763-2764

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