Tables of the Properties of Deoxy Sugars and Their Simple Derivatives

Butterworth, Roger F.; Hanessian, Stephen

doi:10.1016/s0065-2318(08)60369-8

Cited by 25 publications

(7 citation statements)

References 188 publications

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“…On the other hand, the glycosidic bonds of polysaccharides containing hexuronic acids and N-acetylhexosaminuronic acids are extremely more resistant to acids than polysaccharide composed of neutral sugars. Similarly, glycosidic bond involving 2-deoxy-2amino sugars with a free amino group are resistant to acid hydrolysis (Butterworth & Hanessian, 1971;Banoub et al, 1984).…”

Section: Partial Acid Hydrolysismentioning

confidence: 99%

Structural investigation of bacterial lipopolysaccharides by mass spectrometry and tandem mass spectrometry

Banoub

Aneed

Cohen

et al. 2010

Mass Spectrometry Reviews

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Mass spectrometric studies are now playing a leading role in the elucidation of lipopolysaccharide (LPS) structures through the characterization of antigenic polysaccharides, core oligosaccharides and lipid A components including LPS genetic modifications. The conventional MS and MS/MS analyses together with CID fragmentation provide additional structural information complementary to the previous analytical experiments, and thus contribute to an integrated strategy for the simultaneous characterization and correct sequencing of the carbohydrate moiety.

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Section: Partial Acid Hydrolysismentioning

confidence: 99%

Structural investigation of bacterial lipopolysaccharides by mass spectrometry and tandem mass spectrometry

Banoub

Aneed

Cohen

et al. 2010

Mass Spectrometry Reviews

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“…Deoxy sugars with a variety of intriguing biological activities are found ubiquitously in nature (1)(2)(3). These unusual carbohydrates are derived from common sugars by the replacement of one or more hydroxyl groups with hydrogens, and such a substitution generally causes a fundamental change in their characteristics and metabolism.…”

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confidence: 99%

“…The conversion of ribonucleotide to 2-deoxyribonucleotide is a well-documented example; however, a more infrequent occurrence is that of the 3,6-dideoxyhexoses. These distinctive sugars are commonly an important constituent of the O-antigen of lipopolysaccharides (LPSs), 1 which are part of the outer membrane of Gram-negative bacteria (4)(5)(6). It has been shown that the immunological specificities of different Gram-negative strains are mainly determined by the sugars found at the nonreducing end of the O-antigen repeat units where 3,6-dideoxy sugars usually reside (7)(8).…”

mentioning

confidence: 99%

“…Although the precursors of these dideoxy sugars have been well defined and possible routes for their formation have been postulated, the only pathway that has been studied in detail at the enzymatic level is that of CDPascarylose (16). This complex biosynthetic pathway begins with the coupling of glucose 1-phosphate (1) with CTP catalyzed by D-glucose-1-phosphate cytidylyltransferase (E p ) to give CDP-D-glucose (2) (18). This is followed by an intramolecular oxidation-reduction catalyzed by NAD +dependent CDP-D-glucose 4,6-dehydratase (E od ) (19,20).…”

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confidence: 99%

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Mechanistic Studies of the Biosynthesis of Paratose: Purification and Characterization of CDP-paratose Synthase

et al. 1998

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The 3,6-dideoxyhexoses can be found in the cell wall lipopolysaccharide of Gram-negative bacteria, where they have been shown to be the dominant antigenic determinants. All naturally occurring 3,6-dideoxyhexoses, with colitose as the only exception, are biosynthesized via a complex pathway that begins with CDP-d-glucose. Included in this pathway is CDP-paratose synthase, an essential enzyme in the formation of the 3,6-dideoxy sugars, CDP-paratose and CDP-tyvelose. Recently, the gene encoding CDP-paratose synthase in Salmonella typhi, rfbS, has been identified and sequenced [Verma, N., and Reeves, P. (1989) J. Bacteriol. 171, 5694-5701]. On the basis of this information, we have amplified the rfbS gene by polymerase chain reaction (PCR) from S. typhi and cloned this gene into a pET-24(+) vector. Expression and purification of CDP-paratose synthase have allowed us to fully characterize the catalytic properties of this enzyme, which is a homodimeric protein with a preference for NADPH over NADH. It catalyzes the stereospecific hydride transfer of the pro-S hydrogen from the C-4' position of the reduced coenzyme to C-4 of the substrate, CDP-3,6-dideoxy-D-glycero-D-glycero-4-hexulose. The overall equilibrium of this catalysis greatly favors the formation of the reduced sugar product and the oxidized coenzyme. Interestingly, this enzyme also exhibits a high affinity for NADPH with a much smaller dissociation constant (Kia) of 0.005 +/- 0.002 microM compared to the Km of 26 +/- 8 microM for NADPH. While this unusual property complicated the interpretation of the kinetic data, the kinetic mechanism of CDP-paratose synthase as explored by the combination of bisubstrate kinetic analysis, product inhibition studies, and dead-end competitive inhibition studies is most consistent with a Theorell-Chance mechanism. The present study on CDP-paratose synthase, a likely new member of the short-chain dehydrogenase family, represents the first detailed characterization of this type of ketohexose reductase, many of which may share similar properties with CDP-paratose synthase.

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“…Presented are the identification and confirmation of the E3 gene through cloning and overexpression and the culminating purification and unambiguous assignment of homogeneous E3. The nucleotide and translated amino acid sequences of the genuine E3 are also presented.The deoxy sugars, long known as an important class of carbohydrate, are found ubiquitously in nature (7,16,47). They are formally derived from common sugars by the displacement of one or more hydroxyl groups with hydrogens.…”

mentioning

confidence: 99%

CDP-6-deoxy-delta 3,4-glucoseen reductase from Yersinia pseudotuberculosis: enzyme purification and characterization of the cloned gene

Miller

Lei

et al. 1994

J Bacteriol

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The 3,6-dideoxyhexoses, usually confined to the cell wall lipopolysaccharide of gram-negative bacteria, are essential to serological specificity and are formed via a complex biosynthetic pathway beginning with CDP-D-hexoses. In particular, the biosynthesis of CDP-ascarylose, one of the naturally occurring 3,6-dideoxyhexoses, consists of five enzymatic steps, with CDP-6-deoxy-A3'4-glucoseen reductase (E3) participating as the key enzyme in this catalysis. This enzyme has been previously purified from Yersinia pseudotberculosis by an unusual procedure (protocol I) including a trypsin digestion step (0. Han, V. P. Miller, and H.-W. Liu, J. Biol. Chem. 265:8033-8041, 1990). However, the cloned gene showed disparity with the expected gene characteristics, and upon expression, the resulting gene product exhibited no E3 activity. These findings strongly suggested that the protein isolated by protocol I may have been misidentified as E3. A reinvestigation of the purification protocol produced a new and improved procedure (protocol II) consisting of DEAESephacel, phenyl-Sepharose, Cibacron blue A, and Sephadex G-100 chromatography, which eliciently yielded a new homogeneous enzyme composed of a single polypeptide with a molecular weight of 39,000. This highly purified protein had a specific activity nearly 8,000-fold higher than that of cell lysates, and more importantly, the corresponding gene (ascD) was found to be part of the ascarylose biosynthetic cluster. Presented are the identification and confirmation of the E3 gene through cloning and overexpression and the culminating purification and unambiguous assignment of homogeneous E3. The nucleotide and translated amino acid sequences of the genuine E3 are also presented.The deoxy sugars, long known as an important class of carbohydrate, are found ubiquitously in nature (7,16,47). They are formally derived from common sugars by the displacement of one or more hydroxyl groups with hydrogens. Such a substitution generally induces a dramatic alteration of the biological role of the resulting sugar and is responsible for a fundamental change in the metabolism of the product. Particularly notable are the 3,6-dideoxyhexoses found in the lipopolysaccharides (LPS) of gram-negative bacteria (2). Since LPS is the major surface antigen of the gram-negative cell envelope, this class of dideoxyhexose as the nonreducing end group of LPS has been identified as the key antigenic determinant. In addition, they have also been found to contribute to the serological specificity of many immunologically active polysaccharides (5,24,33,46). Inspired by their specific association with LPS and the intriguing nature of their immunological effects, substantial effort has been devoted to exploring their biosynthetic formation (10, 13). However, although the nature of the precursors of these dideoxy sugars has been well defined and possible routes for their formation have been

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Tables of the Properties of Deoxy Sugars and Their Simple Derivatives

Cited by 25 publications

References 188 publications

Structural investigation of bacterial lipopolysaccharides by mass spectrometry and tandem mass spectrometry

Structural investigation of bacterial lipopolysaccharides by mass spectrometry and tandem mass spectrometry

Mechanistic Studies of the Biosynthesis of Paratose: Purification and Characterization of CDP-paratose Synthase

CDP-6-deoxy-delta 3,4-glucoseen reductase from Yersinia pseudotuberculosis: enzyme purification and characterization of the cloned gene

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