Studies on the reductive amination of 3-deoxy-D-manno-octulosonic acid (Kdo).

Abstract:

:Reductive amination of 3-deoxy-D-manno-octulosonic acid (Kdo) with allylamine (AIIN) or 2-(4-aminophenyl)ethylamine (APEA) yields epimer pairs of 2-N-allylamino and 2-N-[2-(4-aminophenyl)ethylamino]-2,3-dideoxy-D-glycero-D-galacto- and -2,3-dideoxy-D-glycero-D-talo-octonic acid. The yields were 50-60% due to reduction of Kdo to the respective polyols as side reaction products. Mass spectrometric analyses proved the amination derivatives to be the expected glycamines. Nuclear magnetic resonance (NMR) studies were performed on 2-N-allylamino-2,3-dideoxyoctonic acid which represents the chain terminus of allylaminated oligosaccharides derived from bacterial lipopolysaccharides (LPS) after acid hydrolysis and reductive allylamination.

journal_name

Glycoconj J

journal_title

Glycoconjugate journal

authors

Grimmecke HD,Brade H

doi

10.1023/a:1006955508077

subject

Has Abstract

pub_date

1998-06-01 00:00:00

pages

555-62

issue

6

eissn

0282-0080

issn

1573-4986

journal_volume

15

pub_type

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