Thioglycosides of 3-Amino-3-deoxy-D-mannose<sup>1</sup>

Wolfrom, M. L.; Horton, Derek; Garg, Hari G.

doi:10.1021/jo01041a033

Cited by 12 publications

(4 citation statements)

References 4 publications

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“…These findings agree with those obtained by application of the elegant chemical methods of Wolfrom and his colleagues (208,209). From graded hydrolysates of a partially desulfated, N -acetylated, and diborane carboxyl reduced heparin, two crystalline disaccharides, (I), O-Q-n-glucopyranosyl (1-+4)-2-amino-2-deo:cy-a-D-glucopyranose hydrochloride, and (II), 0-2amino-2-deoxy-a-n-glucopyranosyl-(1 -+4)-Q-glucopyranose hydrochloride were isolated.…”

Section: �Ucopolysaccharidessupporting

confidence: 92%

Carbohydrate Metabolism

Ashwell¹

1964

Annu. Rev. Biochem.

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This review is not designed as a comprehensive survey of the literature on carbohydrate metabolism, but has been restricted to five major areas of current activity. This restriction has permitted a more detailed consideration of the experimental data in order to provide a more critical basis for evalu ation of the significance of the work reported. NUCLEOTIDE SUGARSAs a result of intense interest during the last several years, a vast array of sugar nucleotides has been isolated and characterized. There has been, however, a marked shift of emphasis towards the study of nucleotide sugar dependent biosynthetic reactions involved in the formation of complex macromolecules. A striking example is seen in the development in knowledge of the structure of the bacterial O-antigenic polysaccharides, discussed in the section on lipopolysaccharides. Two excellent and comprehensive reviews covering the general area of sugar nucleotides and the synthesis of carbohy drates are currently in press (1, 2), and a complete survey of the biosynthetic reactions involved in the formation of deoxysugars has been published recently (3).Isolation and formation of sugar nucleotides.-Recondo & Leloir (4) found the rate of starch biosynthesis in plant tissues to be approximately tenfold greater when adenosine diphosphoglucose was substituted for uridine diphos phoglucose as precursor. This surprising observation prompted a search for supportive evidence that the former was a naturally occurring metabolite. Two such lines of evidence have now been adduced. Espada (5) isolated and partially purified (20-fold) an enzyme from wheat (ADP-glucose pyrophos phorylase) which catalyzes the formation of ADP-glucose and pyrophosphate upon incubation with ATP and glucose-I-phosphate. Resolution of this enzyme from UDP-glucose pyrophosphorylase by diethylaminoethyl cellu lose chromatography clearly established the separate nature of the two enzymes. The second piece of supporting evidence has been the identification of ADP-glucose as a naturally occurring compound (6) . From the alcoholic extract of one kilogram of corn grain, 8 JLmoles were obtained of a substance which behaved similarly to synthetic ADP-glucose upon paper chromatog raphy and electrophoresis. Upon mild acid hydrolysis, 60-70 percent of the 1 This review covers essentially the period from midsummer 1962 through August 1963.2 Among the abbreviations used in this review are: CMP, CDP, CTP (cytidine mono-, di-, and triphosphate); d (deoxy-); GDP (guanosine diphosphate); TDP (thymidine diphosphate); UDP (uridine diphosphate). 101 Annu. Rev. Biochem. 1964.33:101-138. Downloaded from www.annualreviews.org Access provided by University of California -San Francisco UCSF on 12/14/14. For personal use only. Quick links to online content Further ANNUAL REVIEWS

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Section: �Ucopolysaccharidessupporting

confidence: 92%

Carbohydrate Metabolism

Ashwell¹

1964

Annu. Rev. Biochem.

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“…below the stitching), the strip of Whatman No. 1 paper was placed in the empty irrigating trough and solvent poured in. Zones corresponding to the R¡ values cited above were located by cutting 1-cm.…”

Section: Experimental45mentioning

confidence: 99%

“…• Shown herein to be O-a-Dglucopyranosyl-(l -4)-2-amino-2-deoxy-a-D-glucose hydrochloride (I). 1 Shown herein to be 0-(2-amino-2-deoxy-a-D-glucopyranosyl)-…”

mentioning

confidence: 98%

Two Disaccharides from Carboxyl-Reduced Heparin. The Linkage Sequence in Heparin¹

Wolfrom¹,

Vercellotti²,

Horton³

1964

J. Org. Chem.

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Graded acid hydrolysis of partially O-acetylated, partially desulfated, completely carboxyl-reduced, and Nacetylated heparin, under optimal yield conditions, afforded two crystalline amino sugar-containing disaccharides, isolated from the hydrolysate by preparative paper chromatographic techniques. The unit sequence in each disaccharide was proved by hydrolysis of the corresponding alditols, with isolation of the fragments. Evidence for the linkage positions and configuration was provided by color reactions, electrophoretic data, and infrared spectral and molecular rotatory data on the disaccharides, their iV-acetyl and alditol derivatives. Methylation analysis, with isolation of crystalline partially methylated hydrolytic fragments, provided unequivocal confirmatory proof for formulation of the disaccharides, as 0-a-D-glucopyranosyl-( 1 -4)-2-amino-2-deoxy-a-oglucopyranose hydrochloride (I) and 0-2-amino-2-deoxy-a-D-glucopyranosyl-(l -* 4)-a-n-glucopyranose hydrochloride (II). Juxtaposition of the structures of the two disaccharides demonstrates heparin to possess an a-o-(1 -* 4)-linked backbone structure of 2-amino-2-deoxy-D-glucose and n-glucuronic acid units, very probably in an alternating sequence.

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“…This disaccharide has been obtained recently through enzymatic transfer of X-acetylglucosamine to glucose.27 Its (N-unsubstituted) a Isomer was found in hydrolysates of heparin. 28 It is noteworthy that the yield of the Koenigs-Knorr reaction product of V with IX was considerably lower than that of VI. This observation must be attributed to a steric hindrance due to the bulky molecule of the otherwise highly reactive bromide.…”

mentioning

confidence: 93%