The Biosynthesis of Liposidomycin‐like A‐90289 Antibiotics Featuring a New Type of Sulfotransferase

Funabashi, Masanori; Baba, Susumu; Nonaka, Kazuhiro; Hosobuchi, Masahiko; Fujita, Yöko; Shibata, Tomoyuki; Lanen, Steven G. Van

doi:10.1002/cbic.200900665

Cited by 55 publications

(54 citation statements)

References 16 publications

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“…2) (29,30). Additional members of the GlyU-containing nucleoside antibiotics with identified biosynthetic gene clusters include liposidomycins (31), caprazamycins (32), muraymycin (33), muraminomicin (34), and the recently discovered sphaerimicins (35).…”

Section: Capuramycin-type Antibiotics Include A-500359s Frommentioning

confidence: 99%

The Biosynthesis of Capuramycin-type Antibiotics

Cai

Goswami

Yang

et al. 2015

Journal of Biological Chemistry

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Background: Several nucleoside antibiotics contain a uridine-5Ј-carboxamide core of unclear origin. Results: The A-102395 biosynthetic gene cluster was cloned, a genetic system was developed, and three enzymes were characterized in vivo and in vitro. Conclusion: Uridine-5Ј-carboxamide originates from UMP and L-Thr by sequential reactions catalyzed by a dioxygenase and transaldolase. Significance: The results provide the first opportunity to methodically interrogate the biosynthesis of these unusual antibiotics.

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Section: Capuramycin-type Antibiotics Include A-500359s Frommentioning

confidence: 99%

The Biosynthesis of Capuramycin-type Antibiotics

Cai

Goswami

Yang

et al. 2015

Journal of Biological Chemistry

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“…[13] Structureactivity studies with synthesised peptidyl nucleoside analogues revealed that the terminal amino group, the N-methyl-Daba and probably the uridine moiety are most important for the inhibition of translocase I. [14,15] Recently, the identification and analysis of the gene clusters for caprazamycins, [16,17] liposidomycins [18][19][20] and capuramycintype A-500359 [21] has given the first insights into the biosynthesis of the structurally unusual nucleoside antibiotics that target translocase I. However, little is known about the formation of the uridylpeptide-type translocase I inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Identification of a Napsamycin Biosynthesis Gene Cluster by Genome Mining

et al. 2010

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Napsamycins are potent inhibitors of bacterial translocase I, an essential enzyme in peptidoglycan biosynthesis, and are classified as uridylpeptide antibiotics. They comprise an N-methyl diaminobutyric acid, an ureido group, a methionine and two non-proteinogenic aromatic amino acid residues in a peptide backbone that is linked to a 5'-amino-3'-deoxyuridine by an unusual enamide bond. The napsamycin gene cluster was identified in Streptomyces sp. DSM5940 by using PCR probes from a putative uridylpeptide biosynthetic cluster found in S. roseosporus NRRL15998 by genome mining. Annotation revealed 29 hypothetical genes encoding for resistance, regulation and biosynthesis of the napsamycins. Analysis of the gene cluster indicated that the peptide core structure is assembled by a nonlinear non-ribosomal peptide synthetase (NRPS)-like mechanism that involves several discrete single or didomain proteins. Some genes could be assigned, for example, to the synthesis of the N-methyl diaminobutyric acid, to the generation of m-tyrosine and to the reduction of the uracil moiety. The heterologous expression of the gene cluster in Streptomyces coelicolor M1154 resulted in the production of napsamycins and mureidomycins as demonstrated by LC-ESI-MS and MS/MS analysis. The napsamycin gene cluster provides a molecular basis for the detailed study of the biosynthesis of this class of structurally unusual compounds.

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“…The biosynthesis gene clusters for a number of pyrimidine nucleoside antibiotics have been elucidated, including nikkomycin (4,46), polyoxin (8), blasticidin S (13), A-500359s and A-503803s (25), caprazamycin (38), lipisidomycin (39) and its analogue A-90289 (24), pacidamycins (50,60), muraymycin (12), and tunicamycin (9). However, biosynthesis studies for the amicetin group of disaccharide nucleoside antibiotics are not yet available.…”

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Characterization of the Amicetin Biosynthesis Gene Cluster from Streptomyces vinaceusdrappus NRRL 2363 Implicates Two Alternative Strategies for Amide Bond Formation

Zhang

et al. 2012

Appl Environ Microbiol

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ABSTRACTAmicetin, an antibacterial and antiviral agent, belongs to a group of disaccharide nucleoside antibiotics featuring an α-(1→4)-glycoside bond in the disaccharide moiety. In this study, the amicetin biosynthesis gene cluster was cloned fromStreptomyces vinaceusdrappusNRRL 2363 and localized on a 37-kb contiguous DNA region. Heterologous expression of the amicetin biosynthesis gene cluster inStreptomyces lividansTK64 resulted in the production of amicetin and its analogues, thereby confirming the identity of theamigene cluster.In silicosequence analysis revealed that 21 genes were putatively involved in amicetin biosynthesis, including 3 for regulation and transportation, 10 for disaccharide biosynthesis, and 8 for the formation of the amicetin skeleton by the linkage of cytosine,p-aminobenzoic acid (PABA), and the terminal (+)-α-methylserine moieties. The inactivation of the benzoate coenzyme A (benzoate-CoA) ligase geneamiLand theN-acetyltransferase geneamiFled to two mutants that accumulated the same two compounds, cytosamine and 4-acetamido-3-hydroxybenzoic acid. These data indicated that AmiF functioned as an amide synthethase to link cytosine and PABA. The inactivation ofamiR, encoding an acyl-CoA-acyl carrier protein transacylase, resulted in the production of plicacetin and norplicacetin, indicating AmiR to be responsible for attachment of the terminal methylserine moiety to form another amide bond. These findings implicated two alternative strategies for amide bond formation in amicetin biosynthesis.

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The Biosynthesis of Liposidomycin‐like A‐90289 Antibiotics Featuring a New Type of Sulfotransferase

Cited by 55 publications

References 16 publications

The Biosynthesis of Capuramycin-type Antibiotics

The Biosynthesis of Capuramycin-type Antibiotics

Identification of a Napsamycin Biosynthesis Gene Cluster by Genome Mining

Characterization of the Amicetin Biosynthesis Gene Cluster from Streptomyces vinaceusdrappus NRRL 2363 Implicates Two Alternative Strategies for Amide Bond Formation

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