Liquid Chromatography–Electrospray Mass Spectrometry of Tunicamycin-Type Antibiotics

Tsvetanova, Billyana; Price, Neil P. J.

doi:10.1006/abio.2000.4952

Cited by 35 publications

(38 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…S5). MS/MS fragmentation of tunicamycins has been detailed previously (Tsvetanova and Price, 2001;Tsvetanova et al, 2002). Fragmentation of molecular adduct ions give rise to [M-221] + ions by neutral loss of the N-acetylglucosaminyl group (Fig.…”

Section: Lc/ms and Q-tof Ms Analysis Of The Tunicamycin Profiles Of Rmentioning

confidence: 99%

“…Bacillus subtilis was used as an indicator strain for bioassay screening of the S. lividans TK24 recombinants bearing positive cosmids that contained the complete tunicamycin gene cluster (Tsvetanova and Price, 2001). …”

Section: Genomic Library Construction For S Chartreusismentioning

confidence: 99%

“…After fermentation at 30°C for 5 d, samples were purified according to the method of Tsvetanova and Price (2001). A bioassay and LC/MS (Agilent 1100 series LC/MSD Trap system) were used for detection of tunicamycin.…”

Section: Direct Mutation Of Tunl (Target Gene) In the Positive Cosmidmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…1) are a group of structurally related nucleoside antibiotics produced by several Actinomycetes species (Tsvetanova and Price, 2001;Tsvetanova et al, 2002;Price and Tsvetanova, 2007). The structure of tunicamycins consists of uracil, N-acetylglucosamine (GlcNAc), a unique 11-carbon 2-aminodiadose sugar (tunicamine), and an N-acyl chain with variable lengths (Tsvetanova and Price, 2001;Price and Tsvetanova, 2007). Structurally, the naturally occurring tunicamycins family antibiotics, including mycospocidins (Eckardt et al, 1975), streptovirudins (Eckardt et al, 1975;Keenan et al, 1981), MM 19290 (Kenig andReading, 1979) and corynetoxins (Vogel et al, 1981) are all similar except the difference in the N-acyl chain or/and replacement of 5,6-dihydrouracil for the uracil moiety ( Fig.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Characterization of the tunicamycin gene cluster unveiling unique steps involved in its biosynthesis

Chen

Zhai

et al. 2010

Protein Cell

View full text Add to dashboard Cite

Tunicamycin, a potent reversible translocase I inhibitor, is produced by several Actinomycetes species. The tunicamycin structure is highly unusual, and contains an 11-carbon dialdose sugar and an α, β-1″,11′-glycosidic linkage. Here we report the identification of a gene cluster essential for tunicamycin biosynthesis by high-throughput heterologous expression (HHE) strategy combined with a bioassay. Introduction of the genes into heterologous non-producing Streptomyces hosts results in production of tunicamycin by these strains, demonstrating the role of the genes for the biosynthesis of tunicamycins. Gene disruption experiments coupled with bioinformatic analysis revealed that the tunicamycin gene cluster is minimally composed of 12 genes (tunAtunL). Amongst these is a putative radical SAM enzyme (Tun B) with a potentially unique role in biosynthetic carbon-carbon bond formation. Hence, a seven-step novel pathway is proposed for tunicamycin biosynthesis. Moreover, two gene clusters for the potential biosynthesis of tunicamycin-like antibiotics were also identified in Streptomyces clavuligerus ATCC 27064 and Actinosynnema mirums DSM 43827. These data provide clarification of the novel mechanisms for tunicamycin biosynthesis, and for the generation of new-designer tunicamycin analogs with selective/enhanced bioactivity via combinatorial biosynthesis strategies.

show abstract

Section: Lc/ms and Q-tof Ms Analysis Of The Tunicamycin Profiles Of Rmentioning

confidence: 99%

Section: Genomic Library Construction For S Chartreusismentioning

confidence: 99%

Section: Direct Mutation Of Tunl (Target Gene) In the Positive Cosmidmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Characterization of the tunicamycin gene cluster unveiling unique steps involved in its biosynthesis

Chen

Zhai

et al. 2010

Protein Cell

View full text Add to dashboard Cite

show abstract

A Modular Approach to the Total Synthesis of Tunicamycins

2015

Angewandte Chemie

View full text Add to dashboard Cite

The tunicamycins constitute a delicate mimic of the bisubstrate intermediates of N‐acetyl‐D‐hexosamine‐1‐phosphate translocases and thus inhibit bacterial cell‐wall synthesis and the N glycosylation of eukaryotic proteins. An efficient approach to the synthesis of this unique type of nucleoside antibiotics is now reported and features the assembly of five modules in a highly stereoselective and robust manner. A Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)‐catalyzed O and N glycosylation, and final N acylation were used as the key steps.

show abstract

Stereoselective Synthesis of 1,1′‐Disaccharides by Organoboron Catalysis

2020

View full text Add to dashboard Cite

The highly stereoselective synthesis of 1,1'-disaccharides was achieved by using 1,2-dihydroxyglycosyl acceptors and glycosyl donors in the presence of a tricyclic borinic acid catalyst. In this reaction, the complexation of the diols and the catalyst is crucial for the activation of glycosyl donors, as well as for the 1,2-cis-configuration of the products. The anomeric stereochemistry of the glycosyl donor depends on the employed glycosyl donor. Applications of the produced 1,1'disaccharides are also described.

show abstract

Liquid Chromatography–Electrospray Mass Spectrometry of Tunicamycin-Type Antibiotics

Cited by 35 publications

References 20 publications

Characterization of the tunicamycin gene cluster unveiling unique steps involved in its biosynthesis

Characterization of the tunicamycin gene cluster unveiling unique steps involved in its biosynthesis

A Modular Approach to the Total Synthesis of Tunicamycins

Stereoselective Synthesis of 1,1′‐Disaccharides by Organoboron Catalysis

Contact Info

Product

Resources

About