Oxetane δ-Amino Acids: Chemoenzymatic Synthesis of 2,4-Anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonic Acid

Starting from 1,2-O-isopropylidene-D-xylose, methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate (4) was synthesized. Debenzylation and transformation of the primary hydroxyl group yielded methyl 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonate (9). While transesterification of 4 under basic reaction co...

Full description

Saved in:
Bibliographic Details
Published in:Journal of carbohydrate chemistry 2006-05, Vol.25 (2-3), p.187-196
Main Authors: Dias Lucas, Susana, Iding, Hans, Alker, André, Peter Wessel, Hans, Pilar Rauter, Amélia
Format: Article
Language:English
Subjects:
Candida antarctica
Carbohydrate amino acids
Carbohydrate scaffolds
Enzymatic hydrolysis
Oxetanes
δ-Amino acids
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Starting from 1,2-O-isopropylidene-D-xylose, methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate (4) was synthesized. Debenzylation and transformation of the primary hydroxyl group yielded methyl 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonate (9). While transesterification of 4 under basic reaction conditions was straightforward, an analogous reaction with 9 was not successful. After screening of several lipases, the enzymatic transesterification of 9 was achieved with lipase L2 from Candida antarctica to furnish the title compound 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonic acid in excellent yield. The stereochemistry at the oxetane ring was proven by an x-ray structure of the intermediate methyl 2,4-anhydro-5-azido-D-lyxonate.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328300600732485