Peracetylated laminaribiose: preparation by specific degradation of curdlan and its chemical conversion into N-acetylhyalobiuronic acid.
beta-Laminaribiose octaacetate (2b) was prepared in greater than 50% yield from the microbial polysaccharide curdlan by specific degradation with a yeast cell-wall lytic enzyme preparation, Kitalase,and subsequent acetylation. Acetolysis of curdlan also gave alpha-laminaribiose octaacetate (2a) in 27% yield. The usefulness of these peracetates 2a and 2b as starting materials for organic synthesis was shown by converting 2b into N-acetylhyalobiuronic acid (23), the disaccharide repeating unit of hyaluronic acid. The conversion was carried out via a series of reactions, which included azidonitration of the glucal derivative and selective alkylidenation or direct tritylation to discriminate two primary hydroxyl groups existing in the disaccharide intermediates.
Wang
L X
LX
RIKEN, Institute of Physical and Chemical Research, Saitama, Japan.
Sakairi
N
N
Kuzuhara
H
H
D000085:Acetates / Q000737:chemistry* / Q000378:metabolism; D000107:Acetylation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005936:Glucans / Q000737:chemistry* / Q000378:metabolism*; D006026:Glycoside Hydrolases / Q000378:metabolism; D006820:Hyaluronic Acid / Q000737:chemistry*; D008969:Molecular Sequence Data; D011135:Polysaccharides, Bacterial / Q000378:metabolism*; D047071:beta-Glucans
D000085:Acetates; D004187:Disaccharides; D005936:Glucans; D011135:Polysaccharides, Bacterial; D047071:beta-Glucans; C056533:N-acetylhyalobiuronic acid; C073828:laminaribiose octaacetate; C038459:curdlan; D006820:Hyaluronic Acid; D006026:Glycoside Hydrolases; C063425:kitalase