|
type |
Journal Article |
authors |
Hanson, R.L.; Johnston, R.M.; Goldberg, S.L.; Parker, W.L.; Patel, R.N.
|
title |
Enzymatic preparation of 5-hydroxy-L-proline, N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline from (α-N-protected)-L-ornithine using a transaminase or an amine oxidase |
journal |
Enzyme Microb Technol. |
Activity |
2.6.1.36 |
Family |
2.6.1.36.a |
sel |
selected |
ui |
22113015 |
year |
(2011) |
volume |
48 |
number |
6-7 |
pages |
445-53 |
| |
keywords |
doi: 10.1016/j.enzmictec.2011.03.007 |
abstract |
N-Cbz-4,5-dehydro-L-prolineamide or N-Boc-4,5-dehydro-L-prolineamide are alternative key intermediates for the synthesis of saxagliptin, a dipeptidyl peptidase IV (DPP4) inhibitor recently approved for treatment of type 2 diabetes mellitus. An efficient biocatalytic method was developed for conversion of L-ornithine, N-α-benzyloxycarbonyl (Cbz)-L-ornthine, and N-α-tert-butoxycarbonyl (Boc)-L-ornithine to 5-hydroxy-L-proline, N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline, respectively. Rec. Escherichia coli expressing lysine-ε-aminotransferase and rec Pichia pastoris expressing L-ornithine oxidase were used for these conversions. N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline were chemically converted to key intermediates N-Cbz-4,5-dehydro-L-prolineamide and N-Boc-4,5-dehydro-L-prolineamide, respectively. |
last changed |
2017/07/21 12:40 |
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