The structures of sulfomycin I and berninamycin A

Abé, Hiroshi; Kushida, Katsuhiko; Shiobara, Yoshinori; Kodama, Masashi

doi:10.1016/s0040-4039(00)80308-1

Cited by 66 publications

(44 citation statements)

References 6 publications

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“…2), in which long-range correlations appeared from a proton signal at 8.63 ppm (Oxa(3), H-5) to the quaternary carbons at 158.3 ppm (Oxa(3), C-2) and 138.6 ppm (Oxa(3), C-4), from a proton at 8.53 ppm (Thz( 1), H-5) to the carbons at 162.4ppm (Thz(l), C-2) and 148.8 ppm (Thz(l), C-4), and from a proton at 8.45 ppm (Thz(2), H-5) to the carbons at 167.5 ppm (Thz(2), C-2) and 148.8 ppm (Thz(2), C-4). The chemical shifts of the proton and carbon resonances showing these long-range correlations coincided with those of the corresponding signals of the oxazole and thiazole rings in sulfomycin 1 9 ) and AI0255G 10 ) as shown in Fig. 2.…”

Section: Ch3-ch(oh)-ch-nh- Ch3-ch(oh)-ch C-nh- -Ch-nh- and Ch 3 -Csupporting

confidence: 65%

“…Two methyl resonances at 2.57 and 2.56 ppm showed long-range correlations to quaternary carbons at 154.1 ppm (Oxa(l), C-5) and 128.6ppm (Oxa(l), C-4), and 153.4ppm (Oxa(2), C-5), and 129.1 ppm (Oxa(2), C-4), respectively. These correlations, together with a comparison of the 1 H-and 13C-chemical shifts with those of known compounds 9 ) established the presence of two methyloxazole moieties (Fig. 2).…”

Section: Ch3-ch(oh)-ch-nh- Ch3-ch(oh)-ch C-nh- -Ch-nh- and Ch 3 -Cmentioning

confidence: 64%

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Promoinducin, a Novel Thiopeptide Produced byStreptomycessp. SF2741

Yun

Seto

1995

Bioscience, Biotechnology, and Biochemistry

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Section: Ch3-ch(oh)-ch-nh- Ch3-ch(oh)-ch C-nh- -Ch-nh- and Ch 3 -Csupporting

confidence: 65%

Section: Ch3-ch(oh)-ch-nh- Ch3-ch(oh)-ch C-nh- -Ch-nh- and Ch 3 -Cmentioning

confidence: 64%

Promoinducin, a Novel Thiopeptide Produced byStreptomycessp. SF2741

Yun

Seto

1995

Bioscience, Biotechnology, and Biochemistry

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“…4). This 11-gene cluster from Propionibacterium acnes KPA171202 harbors homologs of tclJ-N and encodes a 47-residue peptide, of which the 15 C-terminal residues putatively encode the thiazolylpeptide berninamycin (30). Further bioinformatic searches for gene clusters harboring homologs of both the heterocycle-forming (tclJ/tclN) and the Dha/Dhb-forming (tclK/tclL) genes uncovered 11 additional gene clusters (Fig.…”

Section: Identification Of Additional Gene Clusters Predicted To Encomentioning

confidence: 99%

Thirteen posttranslational modifications convert a 14-residue peptide into the antibiotic thiocillin

Brown

Acker

Clardy

et al. 2009

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

182

169

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The thiazolylpeptides are a family of >50 bactericidal antibiotics that block the initial steps of bacterial protein synthesis. Here, we report a biosynthetic gene cluster for thiocillin and establish that it, and by extension the whole class, is ribosomally synthesized. Remarkably, the C-terminal 14 residues of a 52-residue peptide precursor undergo 13 posttranslational modifications to give rise to thiocillin, making this antibiotic the most heavily posttranslationally-modified peptide known to date.biosynthesis ͉ natural products ͉ thiazolylpeptides

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“…This class has a unique oxazolyl-thiazolyl-pyridine core embedded in a 35-membered (13-residue) peptidyl macrocycle ( Fig. 1) (23)(24)(25). The antibacterial mechanism of TP-1161, recently isolated from a marine Nocardiopsis species (21,22), has not been disclosed, whereas berninamycin is reported to target the 50S ribosome, similar to thiostrepton (26,27).…”

mentioning

confidence: 99%

The posttranslational modification cascade to the thiopeptide berninamycin generates linear forms and altered macrocyclic scaffolds

Malcolmson

Young

Ruby

et al. 2013

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

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Berninamycin is a member of the pyridine-containing thiopeptide class of antibiotics that undergoes massive posttranslational modifications from ribosomally generated preproteins. Berninamycin has a 2-oxazolyl-3-thiazolyl-pyridine core embedded in a 35-atom macrocycle rather than typical trithiazolylpyridine cores embedded in 26-atom and 29-atom peptide macrocycles. We describe the cloning of an 11-gene berninamycin cluster from Streptomyces bernensis UC 5144, its heterologous expression in Streptomyces lividans TK24 and Streptomyces venezuelae ATCC 10712, and detection of variant and incompletely processed scaffolds. Posttranslational maturation in S. lividans of both the wild-type berninamycin prepeptide (BerA) and also a T3A mutant generates macrocyclic compounds as well as linear variants, which have failed to form the pyridine and the macrocycle. Expression of the gene cluster in S. venezuelae generates a variant of the 35-atom skeleton of berninamycin, containing a methyloxazoline in the place of a methyloxazole within the macrocyclic framework.heterologous expression | linear precursors | prepeptide gene replacement

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The structures of sulfomycin I and berninamycin A

Cited by 66 publications

References 6 publications

Promoinducin, a Novel Thiopeptide Produced byStreptomycessp. SF2741

Promoinducin, a Novel Thiopeptide Produced byStreptomycessp. SF2741

Thirteen posttranslational modifications convert a 14-residue peptide into the antibiotic thiocillin

The posttranslational modification cascade to the thiopeptide berninamycin generates linear forms and altered macrocyclic scaffolds

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