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berninamycin A

CAS No.
58798-97-3
Chemical Name:
berninamycin A
Synonyms
Berninamycin;berninamycin A;BerninaMycin, U27810;Alaninamide, L-threonyl-2-[(1Z)-1-amino-1-propen-1-yl]-5-methyl-4-oxazolecarbonyl-2,3-didehydroalanyl-3-methyl-L-threonyl-2-(1-aminoethenyl)-5-methyl-4-oxazolecarbonyl-2,3-didehydroalanyl-6-[2-(1-aminoethenyl)-4-oxazolyl]-5-(4-carboxy-2-thiazolyl)-2-pyridinecarbonyl-2,3-didehydroalanyl-2,3-didehydro...
CBNumber:
CB01361481
Molecular Formula:
C51H51N15O15S
Molecular Weight:
1146.11
MDL Number:
MOL File:
58798-97-3.mol
MSDS File:
SDS
Last updated:2023-05-21 10:59:17

berninamycin A Properties

Melting point >290°
storage temp. Store at -20°C
solubility Soluble in DMSO
form solid
color white
FDA UNII M2B3X4HA2W

berninamycin A price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 18769 Berninamycin A ≥99% 58798-97-3 1mg $287 2024-03-01 Buy
Cayman Chemical 18769 Berninamycin A ≥99% 58798-97-3 5mg $1211 2024-03-01 Buy
TRC B318800 BerninamycinA(~90%) 58798-97-3 1mg $220 2021-12-16 Buy
Usbiological B1078-75 Berninamycin A 58798-97-3 1mg $523 2021-12-16 Buy
TRC B318800 BerninamycinA(~90%) 58798-97-3 5mg $970 2021-12-16 Buy
Product number Packaging Price Buy
18769 1mg $287 Buy
18769 5mg $1211 Buy
B318800 1mg $220 Buy
B1078-75 1mg $523 Buy
B318800 5mg $970 Buy

berninamycin A Chemical Properties,Uses,Production

Uses

Berninamycin A is a cyclic thiopeptide antibiotic first isolated from S. bernensis. It inhibits protein biosynthesis in Gram positive bacteria through binding with ribosomal subunits. Cyclic thiopeptide antibiotics, including berninamycin A, induce the transcriptional activator TipA in Streptomyces.[Cayman Chemical]

Uses

Berninamycin A is an antibiotic discovered in 1976 from a strain of Streptomyces. Berninamycin A is a macrocyclic "peptide" comprising atypical amino acids linked to thiazole and oxazoles. Chemically very complex, berninamycin A is an inducer of tipA, a gene that controls the bacterial transcription regulators, TipAL and TipAS, that are central to multidrug resistance. Berninamycin A is closely related to siomycin, a recently discovered inhibitor of oncogenic transcription factor, FoxM1.

Biological Activity

berninamycin a is a macrocyclic thiopeptide antibiotic first isolated from s. bernensis [1]. thiopeptides are sulfur containing highly modified macrocyclic antibiotics with a central pyridine/tetrapyridine/dehydropiperidine ring with up to three thiazole substituents on positions 2, 3 and 6. thiazole antibiotics thiostrepton behaves as proteasome inhibitor in mammalian tumor cells. berninamycin showed no proteasome inhibitory activity [2]. it has been reported that the action mode of berninamycin on bacterial protein synthesis was related to that of a dissimilar compound thiostrepton. the antibiotics could bind to the complex of 23s rna with protein l11 and both affect multiple functions of the ribosomal a site [3]. berninamycin a was involved in inducing the transcriptional activator tipa in streptomyces [4].

Enzyme inhibitor

This fungal antibiotic (FW = 1146.12 g/mol; CAS 58798-97-3; Soluble in DMSO), also known as Antibiotic U27810, from Streptomyces bernensis inhibits protein biosynthesis by binding to a complex formed by ribosomal 23S and the L11 protein, thereby disrupting the function of the ribosome’s A site and inhibiting protein synthesis in Gram-positive bacteria. In this respect, it has the same mode of action as thiostrepton. Streptomyces bernensis and Streptomyces azureus, which produce berninamycin and thiostrepton, respectively, possess similar ribosomal RNA methylases that mediate specific pentose-directed methylation of 23S ribosomal RNA, rendering the modified ribosomes resistant to these antibiotics.

References

[1] lau r c m, rinehart k l. berninamycins b, c, and d, minor metabolites from streptomyces bernensis[j]. the journal of antibiotics, 1994, 47(12): 1466-1472.
[2] pandit b, bhat u g, gartel a l. proteasome inhibitory activity of thiazole antibiotics[j]. cancer biology & therapy, 2011, 11(1): 43-47.
[3] j. thompson, e. cundliffe and m. j. r. stark. the mode of action of berninamycin and mechanism of resistance in the producing organism, streptomyces bernensis. j.gen.microbiol. 128(4), 875-884 (1982).
[4]. m. l. chiu, m. folcher, t. katoh, et al. broad spectrum thiopeptide recognition specificity of the streptomyces lividans tipal protein and its role in regulating gene expression. the journal of biological chemisty 274(29), 20578-20586 (1999).

berninamycin A Preparation Products And Raw materials

Raw materials

Preparation Products

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berninamycin A Berninamycin BerninaMycin, U27810 Alaninamide, L-threonyl-2-[(1Z)-1-amino-1-propen-1-yl]-5-methyl-4-oxazolecarbonyl-2,3-didehydroalanyl-3-methyl-L-threonyl-2-(1-aminoethenyl)-5-methyl-4-oxazolecarbonyl-2,3-didehydroalanyl-6-[2-(1-aminoethenyl)-4-oxazolyl]-5-(4-carboxy-2-thiazolyl)-2-pyridinecarbonyl-2,3-didehydroalanyl-2,3-didehydro... 58798-97-3 C51H51N15O15S