Industrial Biotransformations

Aminopeptidase
Pseudomonas putida
● The antihypertensive drug L-methyl-DOPA (see page 461) and the herbicide arsenal can be
synthesized using α-alkyl amino acids:
Fig. 3.4.11.1 – 8
6) Literature
NH 2
COOH
D-α-methylvaline
● Crosby, J. (1991) Synthesis of optically active compounds: A large scale perspective, Tetrahedron
47, 4789–4846
● Kamphuis, J., Hermes, H.F.M., van Balken, J.A.M., Schoemaker, H.E., Boesten, W.H.J., Meijer,
E.M., (1990) Chemo-enzymatic synthesis of enantiomerically pure alpha-H and alpha-alkyl
alpha-amino acids and derivates, in: Amino acids: Chemistry, Biology, Medicine; (Lubec, G.,
Rosenthal, G.A., eds.) pp. 119–125, ESCOM Science Pupl., Leiden
● Kamphuis, J., Meijer, E.M., Boesten, W.H.J., Sonke, T., van den Tweel, W.J.J., Schoemaker,
H.E. (1992) New developments in the synthesis of natural and unnatural amino acids, in:
Enzyme Engineering XI, Vol. 672 (Clark, D.S., Estell, D.A., eds.), pp. 510–527, Ann. N. Y.
Acad. Sci.
● Meijer, E.M., Boesten, W.H.J., Schoemaker, H.E., van Balken, J.A.M. (1985) Use of biocatalysts
in the industrial production of speciality chemicals, in: Biocatalysis in Organic Synthesis,
(Tramper, J., Van der Plas, H.C., Linko, P.), eds.) pp. 135–156 Elsevier, Amsterdam, The Netherlands
● Schoemaker, H.E., Boesten, W.H.J., Kaptein, B., Hermes, H.F.M., Sonke, T., Broxterman,
Q.B., van den Tweel, W.J.J., Kamphuis, J. (1992) Chemo-enzymatic synthesis of amino acids
and derivatives, Pure & Appl. Chem. 64, 1171–1175
● Sheldon, R.A. (1993) Chirotechnology, Marcel Dekker, New York
HO
HO
EC 3.4.11.1
● van den Tweel, W.J.J., van Dooren, T.J.G.M., de Jonge, P.H., Kaptein, B., Duchateau, A.L.L.,
Kamphuis, J. (1993) Ochrobactrum anthropi NCIMB 40321: a new biocatalyst with broad-spectrum
L-specific amidase activity, Appl. Microbiol. Biotechnol. 39, 296–300
O
NH 2
OH
L-α-methyl-DOPA (Merck)
N
COOH·NEt 3
N
H
N
O
arsenal (American Cyanamid)
343