Reduction of the Products of Periodate Oxidation of Carbohydrates. I. Hydrogenation with Raney Nickel of the Dialdehydes from the Methyl Glycopyranosides<sup>1</sup>

Smith, Felix T.; Cleve, J. W. Van

doi:10.1021/ja01616a047

Cited by 43 publications

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“…The finding that periodate oxidized the glucose suggested a further approach. Cleavage of the glucose ring and reduction of the resulting dialdehyde would give the extremely acid-labile (Smith & Van Cleve, 1955) acetal of glycolaldehyde (or glyceraldehyde if C-2 was substituted). Hydrolysis of this acetal would remove all glucose carbon atoms from a glucosyl-poly-(glycerol phosphate) without degrading the poly-(glycerol phosphate), but would degrade a poly(glycerol phosphate glucose) to low-molecularweight fragments.…”

Section: Resultsmentioning

confidence: 99%

Teichoic acid synthesis in Bacillus stearothermophilus

Kennedy

1974

Biochemical Journal

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1. Particulate enzyme preparations obtained from Bacillus stearothermophilus B65 by digestion with lysozyme were shown to catalyse teichoic acid synthesis. With CDP-glycerol as sole substrate the preparations synthesized 1,3-poly(glycerol phosphate). It was characterized by alkaline hydrolysis, by glucosylation to the alkali-stable 2-glucosyl-1,3-poly(glycerol phosphate) with excess of UDP-glucose and a Bacillus subtilis Marburg enzyme system, by degradation of this latter product with 60%HF and periodate oxidation of the resulting glucosylglycerol. The specificity of the B. subtilis system previously reported (Glaser & Burger, 1964), was confirmed in the present work. 2. Pulse-labelling experiments, followed by periodate oxidation of the product and isolation of formaldehyde from the glycerol terminus of the polymer, showed that the B. stearothermophilus enzyme system transferred glycerol phosphate units to the glycerol end of the chain. The transfer reaction was irreversible. It was not determined if these poly(glycerol phosphate) chains were synthesized de novo, but it was shown that the newly synthesized oligomers were bound to much larger molecules. 3. When the B. stearothermophilus enzyme system was supplied with both CDP-glycerol and UDP-glucose, 1-glucosyl-2,3-poly(glycerol phosphate) was synthesized in addition to the 1,3-isomer. The former polymer was characterized by acid and alkaline hydrolysis, degradation with HF and periodate oxidation of the resulting glucosylglycerol, and periodate oxidation of the intact polymer followed by mild acid hydrolysis. This latter procedure removed the glucose substituents without disrupting the poly(glycerol phosphate) chain. 4. The poly(glycerol phosphate) isomers were distinguished by glucosylation with the B. subtilis enzymes and alkaline hydrolysis, the 2,3-isomer remaining alkali-labile. The proportion of 2,3-poly(glycerol phosphate) in the product increased with increasing amounts of UDP-glucose in the incubation mixture, but the total glycerol phosphate incorporated into products remained constant. It is suggested that the synthetic pathways of the two poly(glycerol phosphate) species may share a rate-limiting step.

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Section: Resultsmentioning

confidence: 99%

Teichoic acid synthesis in Bacillus stearothermophilus

Kennedy

1974

Biochemical Journal

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“…Glycerol specifically labeled at the C1 of sn-glycerol was prepared by Smith degradation of glucose-6-14C (12 (Fig. 1A).…”

Section: Methodsmentioning

confidence: 99%

Biosynthesis of the covalently linked diglyceride in murein lipoprotein of Escherichia coli.

Chattopadhyay¹,

Wu²

1977

Proc. Natl. Acad. Sci. U.S.A.

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Biosynthesis of the diglyceride moiety of murein lipoprotein in Escherichia coli was studied by pulse-labeling with [2-3Hlglycerol and subsequent chase. The evidence strongly suggests that the precursor of the glycerol moiety in lipoprotein is one of the major phospholipid species in E. coli. Studies of biosynthesis of lipoprotein in cerulenin-treated cells indicated that the nonacylated glycerol moiety of phosphatidylglycerol is the donor for the formation of a thioether linkage in the glycerylcysteine residue of the lipoprotein. This is supported by the observation that carbon 1 rather than carbon 3 of sn-glycerol is involved in this thioether linkage. We propose that the biosynthesis of lipoprotein proceeds as follows: apolipoprotein + phosphatidylglycerol or acyl phosphatidylglycerol lipoprotein + phosphatidic acid.One of the major cell envelope proteins of Escherichia coli is the murein lipoprotein discovered by Braun and Rehn (1). The primary structure of this lipoprotein has been determined (2), and recent studies on the biosynthesis and assembly of murein lipoprotein suggest that the primary translation product of the lipoprotein gene is a polypeptide having an apparent molecular weight of 15,000 (prolipoprotein) (3, 4). One of the posttranslational modifications of the prolipoprotein is the transfer of glycerol or a diglyceride moiety from a precursor to the sulfhydryl group of the cysteine residue which ultimately becomes the NH2-terminal amino acid of the lipoprotein (5).In this paper, we present evidence that strongly suggests that the covalently linked diglyceride in lipoprotein is derived from the nonacylated glycerol-moiety of phosphatidylglycerol. MATERIALS AND METHODSBacterial Strains and Media. E. coli strain LA-2-89 (fabD) was a gift from D. Silbert (6). ABi 157 (arg-, his-, thr-, pro-, leu-) was provided by B. Bachmann. Strain 8 (glpR glpD) was a gift of E. C. C. Lin. Strains RA80 (pss-) and RA800 (pss+) were the gifts of C. R. H. Raetz (7). We are especially grateful to P. Overath and Y. Hirota for providing strains T1GP (ilvmetE-lacI-cls-) and T1OGP (ilv-metE-lacI-cls+) for the present study prior to publication (G. Pluschke, Y. Hirota, and P. Overath, personal communication). M9 minimal medium (8) of phospholipid, and isolation of free and bound forms of lipoprotein were carried out as described (9, 10). Both free and bound forms of lipoproteins were analyzed by sodium dodecyl sulfate/urea/gel electrophoresis (11). To obtain steady-state labeled cell envelope for use as an internal standard for murein lipoprotein, cells were labeled with ['4C]arginine (0.2 ,uCi/ml; specific activity, 309 mCi/mmol) for three to four generations in M9 glucose medium supplemented with required amino acids and arginine (10 jig/ml).Preparation of sn-Glycerol-1-'4C. Glycerol specifically labeled at the C1 of sn-glycerol was prepared by Smith degradation of glucose-6-14C (12 (Fig. 1A). However, after a 60-min chase there was a 6-fold increase in glycerol radioactivity covalently linked to lipoprotein (Fi...

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“…1450) and the glycerol (representing C-4-6 of glucose) was converted into its tri-p-nitrobenzoate (yield 150mg., m.p. 198°) (Smith & Van Cleve, 1955). The radioactivity of samples of the glycerol derivative, the glycol derivative, formic acid and methyl OC-D-glucoside was determined.…”

Section: Methodsmentioning

confidence: 99%

The biosynthesis of streptomycin. The origin of the C-formyl group of streptose

Candy¹,

Baddiley²

1965

Biochemical Journal

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1. The biosynthesis of streptomycin in Streptomyces griseus has been studied by adding d-[3,4-(14)C(2)]glucose or d-[1,3-(14)C(2)]glucose to the growth medium and degrading the streptomycin produced. 2. The results suggest that the C-3' branch carbon atom of l-streptose arises from C-3 of d-glucose. 3. The mechanism of biosynthesis of streptose from glucose is discussed. It probably involves an intramolecular rearrangement of a 6-deoxy-4-oxyhexose derivative, and it is suggested that the nucleoside diphosphate sugar derivative hitherto recognized as an intermediate in the biosynthesis of l-rhamnose might participate in such a rearrangement.

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Reduction of the Products of Periodate Oxidation of Carbohydrates. I. Hydrogenation with Raney Nickel of the Dialdehydes from the Methyl Glycopyranosides¹

Cited by 43 publications

References 0 publications

Teichoic acid synthesis in Bacillus stearothermophilus

Teichoic acid synthesis in Bacillus stearothermophilus

Biosynthesis of the covalently linked diglyceride in murein lipoprotein of Escherichia coli.

The biosynthesis of streptomycin. The origin of the C-formyl group of streptose

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Reduction of the Products of Periodate Oxidation of Carbohydrates. I. Hydrogenation with Raney Nickel of the Dialdehydes from the Methyl Glycopyranosides1

Cited by 43 publications

References 0 publications

Teichoic acid synthesis in Bacillus stearothermophilus

Teichoic acid synthesis in Bacillus stearothermophilus

Biosynthesis of the covalently linked diglyceride in murein lipoprotein of Escherichia coli.

The biosynthesis of streptomycin. The origin of the C-formyl group of streptose

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Reduction of the Products of Periodate Oxidation of Carbohydrates. I. Hydrogenation with Raney Nickel of the Dialdehydes from the Methyl Glycopyranosides¹