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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

Paper ID Volume ID Publish Year Pages File Format Full-Text
17454 42670 2011 9 PDF Available
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
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-ɛ-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.

Keywords
Lysine-ɛ-aminotransferase; Amine oxidase; Pichia; Ornithine; 5-Hydroxyproline
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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
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Publisher
Database: Elsevier - ScienceDirect
Journal: Enzyme and Microbial Technology - Volume 48, Issues 6–7, 6 May 2011, Pages 445–453
Authors
, , , , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us