Abstract
The lipase-catalyzed aminolysis of carboxylic esters is a fairly general reaction that has been performed with a wide range of esters and amines, generally in anhydrous organic media to avoid undesirable hydrolysis of the ester. Alternatively, carboxylic amides can be synthesized by lipase mediated condensation of carboxylic acids and amines if an excess of either reactant is avoided.
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References
Sheldon RA (1997) Chem Ind (London) 12
Sheldon RA (1997) J Chem Technol Biotechnol 68:381
De Zoete MC, Van Rantwijk F, Sheldon RA (1994 Catalysis Today 22: 563
Schmidt RD, Verger R (1998)Angew Chem Int Ed Engl 37: 1608
Inada Y, Nishimura H, Takahashi K, Yoshimoto T, Saha AR, Saito Y (1984) Biochem Biophys Res Commun 122: 845
Zaks A, Klibanov AM (1985) Proc Natl Acad Sci USA 82: 3192
Pleiss J, Fischer M, Schmidt RD (1998)Chem Phys Lipid 93: 67
De Zoete MC, Kock-van Dalen AC, Van Rantwijk F, Sheldon RA (1996)J Mol Catal B: Enzym 2: 19
Gotor V, Brieva R, González C, Rebolledo F (1991)Tetrahedron 47: 9207
Faber K (1997) Biotransformations in Organic Chemistry, 3rd edn. Springer, Berlin, p 92
Ishii M (1988) PCT Int Appl WO 88/02775; Heldt-Hansen HP, Ishii M, Patkar SA, Hansen TT, Eigtved P (1989) In: Whitaker JR, Sonnet PE (eds) Biocatalysis in Agricultural Biotechnology, ACS Symposium Series, vol 389. American Chemical Society, Washington, chap 11, p 158
Anderson EM,Larsson KM,Kirk O(1998)Biocatal Biotransform16: 181
De Goede ATJW, Benckhuysen W, Van Rantwijk F, Maat L, Van Bekkum H (1993) Recl Tray Chim Pays-Bas 112: 567
De Zoete MC, Kock-van Dalen AC, Van Rantwijk F, Sheldon RA (1996) J Mol Catal B: Enzym 2: 19
Wegman MA, Hacking MAPJ, Rops J, Pereia P, Van Rantwijk F, Sheldon RA (1999)Tetrahedron Asymm 10: 1739
[15]Van Rantwijk F, Kock-van Dalen AC, Sheldon RA (1998) in: Ballasteros A, Plou FJ, Iborra JL, Hailing P (eds) Stability and Stabilisation of Enzymes.Progress in Biotechnology,vol 15. Elsevier Science, p 447
Haynes CA, Norde W(1994)Colloids Surf B:Biointerfaces 2: 517
Reetz MT,Zonta A,Simpelkamp J(1995)Angew Chem Int Ed Eng134:301
Reetz MT,Zonta A,Simpelkamp J(1996)Biotechnol Bioeng49: 527
St Clair NL,Navia M (1992)J Am Chem Soc 114:7314;
Margolin AL(1996)Trends Biotechnol 14:223;
Govardhan CP(1999)Curr Opin Biotechnol 10:331
Hacking MAPJ,Van Rantwijk F,Sheldon RA (in prep)
Hacking MAPJ,Akkus H,Van Rantwijk F, Sheldon RA (2000)Biotechnol Bioeng (in press)
Pedersen S,Eigtved P(1990)PCT Int Appl WO 90/15868
GarcÃa MJ,Rebolledo F,Gotor V(1993)Tetrahedron Lett34: 6141
Rebolledo F,Brieva R,Gotor V(1989)Tetrahedron Lett30: 5345;
b Puertas S,Brieva R,Rebolledo F,Gotor V(1993)Tetrahedron49: 4007
It may be a coincidence that the only documented example of lipase catalysed synthesis of phenol esters also involved CrL; see: Abramowicz DA, Keese CR (1987) Biotechnol Bioeng 33: 149
Gotor V, Brieva R, Rebolledo F (1988) J Chem Soc Chem Commun 957;
Fernández S,Brieva R,Rebolledo F,Gotor V (1992)J Chem Soc Perkin Trans1,2885
Quirós M, Rebolledo F, Gotor V (1994) J Chem Res (M) 1917
Acensio G,Andreu C,Marco JA(1991)Tetrahedron Lett32: 4197
Maugard T,Remaud-Simon M,Petre D,Monsan P(1997)Tetrahedron53: 5185;
Maugard T,Remaud-Simon M,Petre D,MonsanP(1997)Tetrahedron53: 7587;
Maugard T,RemaudSimon M,Monsan P(1998)J Mol Catal B: Enzym5: 13;
Maugard T,Remaud-Simon M,Monsan P(1998)Biochim Biophys Acta1387: 177
De Zoete MC, Kock-van Dalen AC, Van Rantwijk F, Sheldon RA (1993) J Chem Soc Chem Commun 1831
De Zoete MC, Kock-van Dalen, AC, Van Rantwijk F, Sheldon RA (1994)Biocatalysis 10: 307
De Zoete MC, Kock-van Dalen AC, Van Rantwijk F, Sheldon RA (1996) xx J Mol Catal B: Enzym 1: 109 (1996) [Erratum: 2: 141]
a Servat F, Monted D, Pina M, Arnaud A, Ledon H, Marcou L, Graille J (1990)J Am Oil Chem Soc 67: 646;
Servat F, Monted D, Pina M, Arnaud A, Galzy P, Graille J, Ledon H, Marcou L (1990) Tenside Surf Det 27:298
Gotor V, Astorga C, Rebolledo F (1990) Synlett 387;
Astorga C, Rebolledo F, Gotor V (1991) Synthesis 350
[34] Astorga C, Rebolledo F, Gotor V (1993) Synthesis 287
[35]Sánchez V, Rebolledo F, Gotor V (1994) Synlett 529
Quirós M, Astorga C, Rebolledo F, Gotor V (1995)Tetrahedron 51: 7715
Chamorro C, Gonzáles -Muñiz R, Conde S (1995)Tetrahedron Asymm 6: 2343
Puerta S, Rebolledo F, Gotor V (1995) Tetrahedron 51: 1495
Conde S, López-Fierros, Fierros M, Biezma MI, MartÃnez A, RodrÃguez-Franco MI (1997) Tetrahedron 53:11745
Gutman AL, Meyer E, Yue X, Abell C (1992)Tetrahedron Lett 33: 3943
Hacking MAPJ, Van Rantwijk F, Sheldon RA (2000)J Mol Catal B: Enzym (in press)
Margolin AL, Klibanov AM (1987)J Am Chem Soc 109: 3802
West JB, Wong C-H (1987)Tetrahedron Lett 28:1629
Kawashiro K, Kaise, K, Minato D, Sugiyama S, Hayashi H (1993) Tetrahedron 21: 4541
So J-E,Kang S-H,Kim B-G(1998)Enzyme Microb Technol 23: 211
Tuccio B,FerréE,Comeau L(1991)Tetrahedron Lett32: 2763
Maugard T,Remaud-Simon M,Petre D,Monsan P,(1997)Biotechnol Lett 19: 751
Litjens MJJ,Straathof AJJ,Jongejan JA,Heijnen JJ(1999)Chem Commun (Cambridge)1255
Litjens MJJ,Sha M,Straathof AJJ,Jongejan JA,Heijnen JJ(1999)Biotechnol Bioeng65:347
Vaysse L,Dubreucq E,Pirat J-L,Galzy P(1997)J Biotechnol53: 41
Hacking MAPJ, Van Rantwijk F, Sheldon RA (2000)J Mol Catal B: Enzym (in press)
Dakin HD(1903)Proc Chem Soc 19:161
Chen C-S,Wu S,Girdaukas G,Sih CJ(1987)J Am Chem Soc109: 2812
Chen C-S,Fujimoto Y,Girdaukas G,Sih CJ(1982)J Am Chem Soc104:7294
Straathof AJJ,Jongejan JA(1997)Enzyme Microb Technol21;559
Anthonson T,Jongejan JA (1997)Solvent Effect in Lipase-Catalyzed Racemate Resolution.In:Rubin B,Dennis EA (eds) Methods in Enzymology,vol 286.Academic Press,New York,p 473
Gotor V, Brieva R, Rebolledo F (1988)Tetrahedron Lett 29: 6973
Rakels JLI, Schneiders AGM, Straathof AJJ, Heijnen JJ (1996)Biocatal Biotransform 13: 179
Kirchner G, Scollar M, Klibanov AM (1985)J Am Chem Soc 107: 7072
Gubicza L (1992) Effect of the Solvent on Enzyme Enantioselectivity. In: Tramper J, Vermüe MH, Beeftink HH, Von Stockar U (eds) Biocatalysis in Non-Conventional Media. Elsevier Science, Amsterdam, p 497
Rakels JLI, Straathof AJJ, Heijnen JJ (1994)Tetrahedron Asymm 5: 93
Starmans WAJ(1997)Synthesis and application of functionalized azetidines,Thesis,Catholic University of Nijmegen,chapter 2
Starmans WAJ, Doppen RG, Thijs L, Zwanenburg B (1998) Tetrahedron Asymm 9: 429
McConville FX, Lopez JL, Wald SA (1990) Enzymatic Resolution of Ibuprofen in a Multiphase Membrane Reactor. In: Abramowicz DA (ed) Biocatalysis. Van Nostrand Reinhold, New York, p 167
De Zoete MC, Ouwehand AA, Van Rantwijk F, Sheldon RA (1995)Reel Tray Chim Pays-Bas 114: 171
Hacking MAPJ, Wegman MA, Rops J, Van Rantwijk F, Sheldon RA (1998)J Mol Catal B: Enzymatic 5:155
Conde S, López-Serrano P, MartÃnez A (1998) Biotechnol Lett 20: 261
Adamczyk M, Grote J, Rege S (1997) Tetrahedron Asymm 8: 2509
Sánchez VM, Rebolledo F, Gotor V (1997)Tetrahedron Asymm 8: 37
GarcÃa MJ, Rebolledo F, Gotor V (1992)Tetrahedron Asymm 3: 1519
GarcÃa MJ, Rebolledo F, Gotor V (1993)Tetrahedrom Asymm 4: 2199
GarcÃa-Urdiales E, Rebolledo F, Gotor V (1999)Tetrahedron Asymm 10: 721
Puertas S, Rebolledo F, Gotor V (1996) J. org Chem 61: 6024
Pozo M, Gotor V (1993)Tetrahedron 49: 10725
Kitaguchi H, Fitzpatrick PA, Huber JE, Klibanov AM (1989) J Am Chem Soc 111: 3094
Ke T, Klibanov AM (1998) J Am Chem Soc 120:4259
Kazlauskas RJ, Weissfloch ANE, Rappaport AT, Cuccia LA (1991) J Org Chem 56: 2656;
Cygler M, Grochulski P, Kazlauskas RJ, Schrag JD, Bouthillier F, Rubin B, Serreqi, AN, Gupta AK (1994)J Am Chem Soc 116: 3180
Kazlauskas RJ (1994) Trends Biotechnol 12: 464 and pertinent references cited in [75b]
Uppenberg J, Öhrner N, Norin M, Hult K, Kleywegt GJ, Patkar S, Waagen V, Anthonson T, Jones TA (1995) Biochemistry 34: 16838
Reetz MT, Dreisbach C (1994) Chimia 48: 570
Jaeger K-E, Liebeton K, Zonta A, Schimosschek K, Reetz MT (1996)Appl Micriobiol Biotechnol 46: 99
Pozo M, Gotor V (1993) Tehrahedron 49: 4321
Öhrner N, Orrenius C, Mattson A, Norin T, Hult K (1996) Enzyme Microbiol Technol 19: 328
[82] Reeve CD (1999) Int Pat Appl WO 99/31264
Takayama S, Lee ST, Hung S-C, Wong C-H (1999) Chem Commun (Cambridge) 127
Balkenbohl F, Ditrich K, Hauer B, Ladner W (1997) J Prakt Chem 339: 381
a Chulalaksananukul W, Condoret JS, Delorme P, Willemot RM (1990)FEBS 276: 181;
Rizzi M, Stylos P, Riek A, Reuss M (1992)Enzyme Microb Technol 14: 709;
Maximo MF, Van der Lugt JP (1994) Biocatalysis 8: 321;
Öhrner N, Martinelle M, Mattson A, Norin T, Hult K (1994) Biocatalysis 9: 105;
De Goede ATJW, Van Oosterom M, Van Deurzen MPJ, Sheldon RA, Van Bekkum H, Van Rantwijk F (1994) xx Biocatalysis 9: 145;
Berglund P, Holmquist M, Hult K, Högberg H-E (1995)Biotechnol Lett 17: 55;
Van der Heijden AM, Zuijderduijn FJ, Van Rantwijk F (1998)J Mol Catal A: Chemical 134: 259.
Reetz MT, Schimossek K (1996)Chimia 50: 668
Messina F, Botta M, Corelli F, Schneider MP, Fazio F (1999) J Org Chem 64: 3767
Nakai K, Hiratake J, Oda J (1992)Inst Chem Res Kyoto Univ 70: 333
[89] Lopez Serrano P, Van Rantwijk F, Sheldon RA (in prep)
Maestro A, Astorga C, Gotor V (1997)Tetrahedron Asymm 8: 3153
[91] Stürmer R (1999) Eur Pat Appl EP 890649 Al
Pozo M, Gotor V (1995)Tetrahedron Asymm 6: 2797
SÃ nchez VM, Rebolledo F, Gotor V (1999)J Org Chem 64: 1464
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van Rantwijk, F., Hacking, A.P.J.M., Sheldon, R.A. (2000). Lipase-Catalyzed Synthesis of Carboxylic. In: Griengl, H. (eds) Biocatalysis. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6310-8_2
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