The Role of Polyisoprenyl Alcohols in the Biosynthesis of the Peptidoglycan of Bacterial Cell Walls and Other Complex Polysaccharides

Strominger, Jack L.; Higashi, Yutaro; Sandermann, Heinrich; Stone, K. J.; Willoughby, Eileen

doi:10.1016/b978-0-12-557250-7.50012-x

Cited by 14 publications

(6 citation statements)

References 47 publications

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“…This supports the presence of a monophosphate, link between the isoprenoid and the sugar residue and coupled with the release, on acid treatment, of mannose but not dimannan, it is also consistent with the idea that a single sugar residue is attached to the polyprenol monophosphate (see e.g. [21] ).…”

Section: Reducing Sugar and Phosphate Determinationssupporting

confidence: 85%

The unambiguous characterization of dolichol phosphate mannose as a product of mannosyl transferase in pig liver endoplasmic reticulum

Evans

Hemming

1973

FEBS Letters

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Section: Reducing Sugar and Phosphate Determinationssupporting

confidence: 85%

The unambiguous characterization of dolichol phosphate mannose as a product of mannosyl transferase in pig liver endoplasmic reticulum

Evans

Hemming

1973

FEBS Letters

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“…Effect of Bacitracin on Glycoprotein Structure and Cell Morphology. Glycosylation of at least some of the glycoproteins of eukaryotic cells occurs via lipid-linked intermediates (17,18) similar to those involved in peptidoglycan synthesis (19); this . In addition, growth of H. salinarium is inhibited by bacitracin (4), an antibiotic that stops peptidoglycan synthesis in normal bacteria by complexing with the lipid pyrophosphate released after transfer of the lipid-linked subunit to the growing peptidoglycan chain (20,21), thus making the carrier lipid unavailable for formation and transfer of additional subunits.…”

Section: Resultsmentioning

confidence: 99%

Structural (shape-maintaining) role of the cell surface glycoprotein of Halobacterium salinarium.

Mescher¹,

Strominger²

1976

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

135

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“…Lipid-bound oligosaccharide phosphates have also been isolated (3,7,8,9). Similar compounds found in bacterial and plant systems are involved in the formation of other complex glycans (10).…”

mentioning

confidence: 99%

Enzymatic Utilization of P ¹ -Di- N -acetylchitobiosyl P ² -Dolichyl Pyrophosphate and Its Chemical Synthesis

Wedgwood

Warren

Jeanloz

et al. 1974

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

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Fully acetylated chitobiose was treated with phosphoric acid to give a mixture of products from which 2-acetamido-4-0-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-fB-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy -a,#-D-glucopyranosyl phosphate (Ac3GlcNAc-Ac2GlcNAc-P) was isolated by preparative thin layer chromatography.Treatment of this compound with P1-diphenyl P2-dolichyl pyrophosphate gave an acetylated pyrophosphate diester, which was purified chromatographically and deacetylated.The product, P'-di-N-acetylchitobiosyl P2-dolichyl pyrophosphate (Dol-P-P-GlcNAc-GlcNAc), was readily separated from P'-2-acetamido-2-deoxy-a-D.glucopyranosyI P2-dolichyl pyrophosphate (Dol-P-P-GlcNAc) by thin layer chromatography in several solvent systems. Addition of this compound to human lymphocyte membrane preparations led to the formation of a mannose-containing derivative which appears to be an oligosaccharide phospholipid, as judged by its behavior on DEAE-cellulose chromatography and by its hydrolysis to give an oligosaccharide containing more than four monosaccharide units.Incubations of membrane preparations from a variety of animal sources with nucleoside diphosphate sugar compounds give glycosyl polyprenyl phosphates, which are intermediates in the biosynthesis of some glycoproteins (1-3). Dolichyl f-Dmannopyranosyl phosphate (Dol-P-Man) has been identified as a product of the incubation with GDP-Man in calf pancreas and in human lymphocytes (4). Dol-P-P-GlcNAc has been shown to be formed from UDP-GlcNAc in calf pancreas (5). Rat liver microsomes have been shown to synthesize lipid-linked pyrophosphate diesters of GlcNAc and di-Nacetylchitobiose (6). Lipid-bound oligosaccharide phosphates have also been isolated (3,7,8,9). Similar compounds found in bacterial and plant systems are involved in the formation of other complex glycans (10).It has been suggested that a mannose-containing oligosaccharide lipid is formed by the transfer of mannose from Abbreviations: GlcNAc-P, 2-acetamido-2-deoxy-D-glucopyranosyl phosphate; Ac3GlcNAc-P, 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl phosphate; Ac3GlcNAc-Ac2GlcNAc-P and GlcNAc-GlcNAc-P, peracetyl-and di-N-acetyl-a,,2-chitobiosyl phosphates, respectively; Dol-P, dolichyl phosphate; Dol-P-Man, dolichyl f3-D-mannopyranosyl phosphate; Dol-P-P, dolichyl pyrophosphate; Dol-P-P-GlcNAc, PL-2-acetamido-2-deoxy-a-D-glucopyranosyl P2-dolichyl pyrophosphate; Dol-P-P-GlcNAc-GlcNAc, PL-di-N-acetylchitobiosyl P2-dolichyl pyrophosphate [P'-2-acetamido-4-0-(2-acetamido-2-deoxy-j3-Dglucopyranosyl)-2-deoxy-a,j2-D-glucopyranosyl P2-dolichyl pyro GDP-Man or Dol-P-Man to Dol-P-P-GlcNAc-GlcNAc (8). An authentic sample of Dol-P-P-GlcNAc-GlcNAc has been obtained by chemical synthesis. This compound stimulates the incorporation, in human lymphocyte membrane preparations, of mannose into a compound with the properties of an oligosaccharide phospholipid containing more than four monosaccharide units. A similar oligosaccharide phospholipid, which contains GlcNAc as well as mannose, is formed when...

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The Role of Polyisoprenyl Alcohols in the Biosynthesis of the Peptidoglycan of Bacterial Cell Walls and Other Complex Polysaccharides

Cited by 14 publications

References 47 publications

The unambiguous characterization of dolichol phosphate mannose as a product of mannosyl transferase in pig liver endoplasmic reticulum

The unambiguous characterization of dolichol phosphate mannose as a product of mannosyl transferase in pig liver endoplasmic reticulum

Structural (shape-maintaining) role of the cell surface glycoprotein of Halobacterium salinarium.

Enzymatic Utilization of P ¹ -Di- N -acetylchitobiosyl P ² -Dolichyl Pyrophosphate and Its Chemical Synthesis

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The Role of Polyisoprenyl Alcohols in the Biosynthesis of the Peptidoglycan of Bacterial Cell Walls and Other Complex Polysaccharides

Cited by 14 publications

References 47 publications

The unambiguous characterization of dolichol phosphate mannose as a product of mannosyl transferase in pig liver endoplasmic reticulum

The unambiguous characterization of dolichol phosphate mannose as a product of mannosyl transferase in pig liver endoplasmic reticulum

Structural (shape-maintaining) role of the cell surface glycoprotein of Halobacterium salinarium.

Enzymatic Utilization of P 1 -Di- N -acetylchitobiosyl P 2 -Dolichyl Pyrophosphate and Its Chemical Synthesis

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Enzymatic Utilization of P ¹ -Di- N -acetylchitobiosyl P ² -Dolichyl Pyrophosphate and Its Chemical Synthesis