Hyalobiuronic acid

Cristalline Disaccharide, Hyalobiuronic Acid from Hyaluronic Acid. Nature [London] 168, 996 (1951). 

The Structure of Hyalobiuronic Acid and of Hyaluronic Acid from... 

Figure 1 Polymeric HA, its degradation product, and methyl hyalobiuronic acid.

Subsequently, Jeanloz and Flowers reported the synthesis of methyl hyalobiuronic acid (II.3) by condensation of l-bromo-2,3,4,6-tetra-0-acetyl-a-D-glucopy-ranoside (II.4) with II.5 in the presence of mercuric cyanide [Hg(CN)2], followed by deacetylation to produce II.6 (Scheme 5). Removal of the 4,6-O-benzylidene with acid afforded II.7, methyl 2-acetamido-2-deoxy-3-0- (j8-D-glucopyranosyl)-a-D-glu-copyranoside, in 35% yield. Attempts to selectively oxidize C6 of the D-glucose moiety in II.7 to the corresponding carboxylic acid with platinum oxide proved unsuccessful. 

Scheme 5 The initial attempt to synthesize hyalobiuronic acid.

Meyer K, Palmer JW, Smyth EM. Glycoproteins. II. The polysaccharides of vitreous humor and of umbilical cord. J Biol Chem 1936 114 689-703. Weissman B, Meyer K. The structure of hyalobiuronic acid and of hyaluronic acid from umbilical cord. J Am Chem Soc 1954 76 1753-1757. 

Weissmann B, Meyer K. The structure of hyalobiuronic acid and of hyalnronic acid from umbilical cord. J Am Chem Soc 1954 76 1753-1757. 

Amino-2-deoxy-3-0-P-D-glucopyranuro-nosyl-D-glucose, 9CI, SCI. Hyalobiuronic acid. P-D-Glucopyranuronosyl-(1 3)-2-amino-2-deoxy-D-glucose [499-15-0]... 

Human milk octasaccharide, H-126 Humatin, P-13 Humaycin, P-13 Hyalbiuronic acid, H-127 Hyalgan, H-128 Hyalobiuronic acid, H-127 Hyaluronan, H-128 Hyaluronate sodium, H-128... 

Jeanloz RW, Flowtas HM (1962) Isolation and synthesis of methyl ester-methyl a-glycoside of 3-P-D-glucurraiosyl-N-acetyl-D-glucosamine (hyalobiuronic acid). J Am Chem Soc 84 3030... 

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