Characterization of three intermediates in the biosynthesis of teichuronic acid of Micrococcus luteus

Johnson, Gary L.; Hoger, J H; Ratnayake, J H; Anderson, John S.

doi:10.1016/0003-9861(84)90244-3

Cited by 13 publications

(10 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The determination that N-acetylglucosamine occurs at the reducing end of teichuronic acid is in agreement with the order of incorporation of saccharide residues demonstrated by in vitro biosynthesis and verifies the fidelity of the in vitro system for biosynthesis of teichuronic acid (14,31).…”

Section: Discussionsupporting

confidence: 79%

“…A technical complication of this experiment is the pH dependence of the competing reactions of saccharide reduction, a-elimination of the reducing terminal residue, and instability of the borohydride. Since the presumed reducing terminal N-acetylglucosamine residue of teichuronic acid is glycosidically substituted at position 3 (10,14), careful pH control is essential to ensure that it does not undergo p-elimination before reduction by the borohydride. A preliminary experiment showed that teichuronic acid maintained at pH 10.5 at room temperature overnight underwent ,3-elimination as indicated by a Sephadex G-10 column separation of Morgan-Elson-positive material from teichuronic acid, whereas teichuronic acid maintained at pH 8.5 or 6.5 gave no evidence of p-elimination.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, there does not seem to be any obvious correlation between the demonstration of synthesis of Dglucosyl polyisoprenyl diphosphate and the attachment site of teichuronic acid to peptidoglycan. Furthermore, the same reasoning strongly suggests that all the linkage points probably involve N-acetylglucosamine residues rather than a combination of N-acetylglucosamine and glucose residues, since it seems unlikely that the initiation of teichuronic acid biosynthesis would occur by two parallel pathways, one already well defined which utilizes UDP-N-acetylglucosamine to introduce the reducing terminal N-acetylglucosamine residue (14,31) and one which would introduce a glucose residue as the reducing terminal residue.…”

Section: Discussionmentioning

confidence: 99%

“…Evidence presented by Hase and Matsushima (10) indicated instead that the reducing end residue is N-acetylglucosamine. Our studies of in vitro teichuronic acid biosynthesis (14,31) showed that biosynthesis depends on the initial step which incorporated N-acetylglucosamine-1-phosphate into a carrier lipid-activated intermediate. Furthermore, the N-acetylglucosamine residue remains in product teichuronic acid at the reducing end, suggesting that teichuronic acid in native cell walls has an N-acetylglucosamine residue at its potentially reducing terminal residue.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Teichuronic acid reducing terminal N-acetylglucosamine residue linked by phosphodiester to peptidoglycan of Micrococcus luteus

et al. 1990

View full text Add to dashboard Cite

Teichuronic acid-peptidoglycan complex isolated from Micrococcus luteus cells by lysozyme digestion in osmotically stabilized medium was treated with mild acid to cleave the linkage joining teichuronic acid to peptidoglycan. This labile linkage was shown to be the phosphodiester which joins N-acetylglucosamine, the residue located at the reducing end of the teichuronic acid, through its anomeric hydroxyl group to a 6-phosphomuramic acid, a residue of the glycan strand of peptidoglycan. 31P nuclear magnetic resonance spectroscopy of the lysozyme digest of cell walls demonstrated the presence of a phosphodiester which was converted to a phosphomonoester by the conditions which released teichuronic acid from cell walls. Reduction of acid-liberated reducing end groups by NaB3H4 followed by complete acid hydrolysis yielded [3H] glucosaminitol from the true reducing end residue of teichuronic acid and [3H]glucitol from the sites of fragmentation of teichuronic acid. The amount of N-acetylglucosamine detected was approximately stoichiometric with the amount of phosphate in the complex. Partial fragmentation of teichuronic acid provides an explanation of the previous erroneous identification of the reducing end residue.Micrococcus luteus cell walls consist of a peptidoglycan matrix to which teichuronic acid is covalently attached (2,8,12,13,29). Although the structure of the disaccharide repeat unit of teichuronic acid has been determined by chemical procedures (9) and confirmed by 13C nuclear magnetic resonance (NMR) spectroscopy (15), the precise nature of the linkage of teichuronic acid to peptidoglycan has remained in dispute. A small amount of phosphate is present in M. luteus cell walls (2), and much of it can be recovered from strong acid hydrolysates as muramic acid-6-phosphate (24). Glucosamine-6-phosphate has also been detected (18,27). A phosphodiester has been suggested as part of the covalent link between peptidoglycan and teichuronic acid in M. luteus (10,25,26) just as it serves to link teichoic acids and other cell wall polymers to peptidoglycan in other microorganisms (4,16,17,19,23).Nasir-ud-Din and Jeanloz (25) claimed that glucose is the reducing end residue of teichuronic acid which links to peptidoglycan through the phosphodiester. Later Nasirud-Din et al. (26) reported experimental results which purported to show that glucose is the reducing end residue of teichuronic acid. Evidence presented by Hase and Matsushima (10) indicated instead that the reducing end residue is N-acetylglucosamine. Our studies of in vitro teichuronic acid biosynthesis (14, 31) showed that biosynthesis depends on the initial step which incorporated N-acetylglucosamine-1-phosphate into a carrier lipid-activated intermediate. Furthermore, the N-acetylglucosamine residue remains in product teichuronic acid at the reducing end, suggesting that teichuronic acid in native cell walls has an N-acetylglucosamine residue at its potentially reducing terminal residue.We report here that the true reducing end residue of teichuronic ...

show abstract

Section: Discussionsupporting

confidence: 79%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Teichuronic acid reducing terminal N-acetylglucosamine residue linked by phosphodiester to peptidoglycan of Micrococcus luteus

et al. 1990

View full text Add to dashboard Cite

show abstract

“…Biosynthesis of teichuronic acid catalyzed by cytoplasmic membrane fragments of M. luteus requires uridine diphosphate D-glucose (UDP-glucose), uridine diphosphate Nacetyl-D-mannosaminuronic acid (UDP-ManNAcA), and uridine diphosphate N-acetyl-D-glucosamine (6,8). Elongation of endogenous teichuronic acid by wall membrane preparations requires only UDP-glucose and UDP-ManNAcA (15).…”

mentioning

confidence: 99%

Biosynthetic elongation of isolated teichuronic acid polymers via glucosyl- and N-acetylmannosaminuronosyltransferases from solubilized cytoplasmic membrane fragments of Micrococcus luteus

Hildebrandt

Anderson

1990

J Bacteriol

View full text Add to dashboard Cite

Cytoplasmic membrane fragments of Micrococcus luteus catalyze in vitro biosynthesis of teichuronic acid from uridine diphosphate D-glucose (UDP-glucose), uridine diphosphate N-acetyl-D-mannosaminuronic acid (UDP-ManNAcA), and uridine diphosphate N-acetyl-D-glucosamine. Membrane fragments solubilized with Thesit (dodecyl alcohol polyoxyethylene ether) can utilize UDP-glucose and UDP-ManNAcA to effect elongation of teichuronic acid isolated from native cell walls. When UDP-glucose is the only substrate supplied, the detergent-solubilized glucosyltransferase incorporates a single glucosyl residue onto each teichuronic acid acceptor. When both UDP-glucose and UDP-ManNAcA are supplied, the glucosyltransferase and the N-acetylmannosaminuronosyltransferase act cooperatively to elongate the teichuronic acid acceptor by multiple additions of the disaccharide repeat unit. As shown by polyacrylamide gel electrophoresis, lowmolecular-weight fractions of teichuronic acid are converted to higher-molecular-weight polymers by the addition of as many as 17 disaccharide repeat units.

show abstract

Teichoic and Teichuronic Acids from Gram‐Positive Bacteria

et al. 2002

View full text Add to dashboard Cite

Introduction Historical Outline Chemical Structures Cell Wall Teichoic Acid Teichuronic Acids Biosynthesis and Genetics of Poly(GroP) Polymerizing Enzyme System for Poly(Glycerol Phosphate) Teichoic Acid The Genetic Basis of the Biosynthesis of the Soluble Precursors Transcriptional Regulation of Wall Teichoic Acid Genes in B. subtilis 168 Biosynthesis and Genetics of Poly (3‐ O ‐β‐D‐Glucopyranosyl N‐Acetylgalactosamine 1‐Phosphate) Genetic and Biochemical Analysis of Mutants Genes Involved in Synthesis of Soluble Precursors UDPGalNAc Genetics of Polymerizing Enzyme System Biosynthesis and Genetics of the B. subtilis 168 Cell Wall Teichuronic Acids Biodegradation Biological Roles Associated with Cell Wall Teichoic and Teichuronic Acids Horizontal Transfer of Genes for Wall Teichoic Acid Synthesis Role of the D‐Alanine Substituent of Wall Teichoic Acid and of the Overall Cell Wall Negative Charge The pH Gradient Across the Cell Wall Cell Wall Teichoic Acid and Upkeep of the Cell Shape Applications

show abstract

Characterization of three intermediates in the biosynthesis of teichuronic acid of Micrococcus luteus

Cited by 13 publications

References 44 publications

Teichuronic acid reducing terminal N-acetylglucosamine residue linked by phosphodiester to peptidoglycan of Micrococcus luteus

Teichuronic acid reducing terminal N-acetylglucosamine residue linked by phosphodiester to peptidoglycan of Micrococcus luteus

Biosynthetic elongation of isolated teichuronic acid polymers via glucosyl- and N-acetylmannosaminuronosyltransferases from solubilized cytoplasmic membrane fragments of Micrococcus luteus

Teichoic and Teichuronic Acids from Gram‐Positive Bacteria

Contact Info

Product

Resources

About