Studies of Aminosugars. XVII. Production of 3-Amino-3-deoxy-<scp>d</scp>-glucose by Bacillus Species

Umezawa, Sumio; Umino, Kimio; Shibahara, Seiji; Omoto, Shoji

doi:10.1246/bcsj.40.2419

Cited by 13 publications

(10 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…by Umezawa and colleagues and found to involve dehydrogenation and transamination of UDP-glucose followed by hydrolysis of the presumed intermediate, UDP-kanosamine. [149][150][151] Preliminary evidence suggests a similar pathway in A. mediterranei. Guo and Frost demonstrated formation of UDP-kanosamine from UDP-glucose by Am.…”

Section: )mentioning

confidence: 99%

Recent Developments in the Maytansinoid Antitumor Agents

et al. 2004

View full text Add to dashboard Cite

Section: )mentioning

confidence: 99%

Recent Developments in the Maytansinoid Antitumor Agents

et al. 2004

View full text Add to dashboard Cite

“…However, the authors were not able to verify this second pathway (6). More recently, we have shown that the ntd operon from Bacillus subtilis expresses three enzymes (NtdA, NtdB, and NtdC) that catalyze the biosynthesis of kanosamine from glucose 6-phosphate in a manner similar to the second pathway proposed for B. pumilus (1,5,6).…”

mentioning

confidence: 94%

“…Kanosamine is a sugar antibiotic shown to inhibit plant pathogens, growth of Saccharomyces cerevisiae, and a range of human pathogenic fungi, including Candida albicans (2)(3)(4). Kanosamine biosynthesis was first observed in Bacillus pumilus (5,6). Various microbes have been found to produce kanosamine as a biosynthetic end product or as an intermediate of other natural products (3,5,(7)(8)(9).…”

mentioning

confidence: 99%

“…Kanosamine biosynthesis was first observed in Bacillus pumilus (5,6). Various microbes have been found to produce kanosamine as a biosynthetic end product or as an intermediate of other natural products (3,5,(7)(8)(9). Kanosamine and UDP-kanosamine are specific intermediates in the biosynthesis of 3-amino-5-hydroxybenzoate, a precursor of the mitomycin and ansamycin antibiotics, including rifamycin B (10).…”

mentioning

confidence: 99%

See 1 more Smart Citation

The Structure of NtdA, a Sugar Aminotransferase Involved in the Kanosamine Biosynthetic Pathway in Bacillus subtilis, Reveals a New Subclass of Aminotransferases

Straaten

Jagdhane

et al. 2013

Journal of Biological Chemistry

View full text Add to dashboard Cite

Background: NtdA represents a novel aminotransferase recognizing a sugar 6-phosphate. Results: We have determined the structure of NtdA with pyridoxamine phosphate (the internal and external aldimines), identifying determinants of substrate specificity. Conclusion: The structures suggest a canonical aminotransferase chemical mechanism, but features exclude the binding of sugar nucleotides. Significance: A new subfamily of sugar aminotransferases is revealed, enhancing our understanding of antibiotic biosynthesis.

show abstract

“…kanosamine) and 3-amino-3,6-dideoxyhexoses (e.g. mycosamine), evidence indicates that the nitrogen donor is glutamine, with an NAD-dependent transaminase acting on the XDP-3-keto-sugar intermediate (61,62). Thus, a possible route to rhizoaminuronic acid could involve C6 oxidation of an XDP-3-aminohexose intermediate.…”

Section: Discussionmentioning

confidence: 99%

Structural Characterization of the Primary O-antigenic Polysaccharide of the Rhizobium leguminosarum 3841 Lipopolysaccharide and Identification of a New 3-Acetimidoylamino-3-deoxyhexuronic Acid Glycosyl Component

Forsberg

Carlson

2008

Journal of Biological Chemistry

View full text Add to dashboard Cite

Rhizobium are Gram-negative bacteria that survive intracellularly, within host membrane-derived plant cell compartments called symbiosomes. Within the symbiosomes the bacteria differentiate to bacteroids, the active form that carries out nitrogen fixation. The progression from free-living bacteria to bacteroid is characterized by physiological and morphological changes at the bacterial surface, a phase shift with an altered array of cell surface glycoconjugates. Lipopolysaccharides undergo structural changes upon differentiation from the free living to the bacteroid (intracellular) form. The array of carbohydrate structures carried on lipopolysaccharides confer resistance to plant defense mechanisms and may serve as signals that trigger the plant to allow the infection to proceed. We have determined the structure of the major O-polysaccharide (OPS) isolated from free living Rhizobium leguminosarum 3841, a symbiont of Pisum sativum, using chemical methods, mass spectrometry, and NMR spectroscopy analysis. The OPS is composed of several unusual glycosyl residues, including 6-deoxy-3-O-methyl-D-talose and 2-acetamido-2-deoxy-L-quinovosamine. In addition, a new glycosyl residue, 3-acetimidoylamino-3-deoxy-D-gluco-hexuronic acid was identified and characterized, a novel hexosaminuronic acid that does not have an amino group at the 2-position. The OPS is composed of three to four tetrasaccharide repeating units of 34The unique 3-amino hexuronate residue, rhizoaminuronic acid, is an attractive candidate for selective inhibition of OPS synthesis.Rhizobium leguminosarum is a Gram-negative endosymbiont that forms a nitrogen-fixing symbiosis with the legume host Pisum sativum. Like other Rhizobiaceae, it is a member of the ␣-2 subgroup of the Proteobacteria, which includes the phytopathogen Agrobacterium and phylogenetically related bacteria such as the intracellular animal pathogens Bartonella and Brucella (1, 2). A significant feature shared by members of this subgroup is the ability to survive intracellularly within the eukaryotic host, often surrounded by host membrane-derived compartments, which in the case of rhizobia are termed symbiosomes.Although the early stages of symbiotic infection have been studied, factors enabling rhizobia to survive within the host cell environment throughout their life cycle are poorly understood (2-7). This is due in part to the difficulty in obtaining sufficient quantities of purified bacteroid mass to allow structural study of components. A model for symbiotic infection begins with a mutual exchange of signal molecules, including inter alia plant flavonoids and bacterial lipochitooligosaccharides, leading to bacterial adhesion to root hairs and the induction of unique plant-derived structures, e.g. root nodules, infection threads, and symbiosomes (2, 8). Rhizobia migrate through the infection threads and are internalized into the root cortical cells through a process resembling endocytosis. Internalization yields symbiosomes, specialized intracellular compartments composed of a plant-d...

show abstract

Studies of Aminosugars. XVII. Production of 3-Amino-3-deoxy-d-glucose by Bacillus Species

Cited by 13 publications

References 4 publications

Recent Developments in the Maytansinoid Antitumor Agents

Recent Developments in the Maytansinoid Antitumor Agents

The Structure of NtdA, a Sugar Aminotransferase Involved in the Kanosamine Biosynthetic Pathway in Bacillus subtilis, Reveals a New Subclass of Aminotransferases

Structural Characterization of the Primary O-antigenic Polysaccharide of the Rhizobium leguminosarum 3841 Lipopolysaccharide and Identification of a New 3-Acetimidoylamino-3-deoxyhexuronic Acid Glycosyl Component

Contact Info

Product

Resources

About