Berninamycin A

Berninamycin A is a macrocyclic thiopeptide antibiotic first isolated from S. bernensis . 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 . 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 . Berninamycin A was involved in inducing the transcriptional activator TipA in Streptomyces .

Product information

CAS Number: 58798-97-3

Molecular Weight: 1146.11

Formula: C51H51N15O15S

Chemical Name: N-(1-carbamoyleth-1-en-1-yl)-2-{[(14S,17Z,27S)-17-ethylidene-14-[(1R)-1-hydroxyethyl]-27-(2-hydroxypropan-2-yl)-20,33-dimethyl-24,30,37,40-tetramethylidene-12,15,22,25,28,35,38-heptaoxo-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecaazahexacyclo[39.2.1.1⁸,¹¹.1¹⁸,²¹.1³¹,³⁴.0²,⁷]heptatetraconta-1(43),2,4,6,8(47),10,18(46),20,31(45),33,41(44)-undecaen-4-yl]formamido}prop-2-enamide

Smiles: C[C@@H](O)[C@@H]1NC(=O)C2=CSC(=N2)C2=CC=C(N=C2C2=COC(=N2)C(=C)NC(=O)C(=C)NC(=O)C2N=C(OC=2C)C(=C)NC(=O)[C@@H](NC(=O)C(=C)NC(=O)C2N=C(OC=2C)/C(=C/C)/NC1=O)C(C)(C)O)C(=O)NC(=C)C(=O)NC(=C)C(N)=O

InChiKey: CAFFHXXVDGAVPH-DKFXDEMXSA-N

InChi: InChI=1S/C51H51N15O15S/c1-13-28-49-65-34(26(10)81-49)45(76)56-21(5)40(71)66-36(51(11,12)78)46(77)58-23(7)48-64-33(25(9)80-48)44(75)55-20(4)39(70)57-22(6)47-61-30(16-79-47)35-27(50-62-31(17-82-50)42(73)63-32(24(8)67)43(74)60-28)14-15-29(59-35)41(72)54-19(3)38(69)53-18(2)37(52)68/h13-17,24,32,36,67,78H,2-7H2,1,8-12H3,(H2,52,68)(H,53,69)(H,54,72)(H,55,75)(H,56,76)(H,57,70)(H,58,77)(H,60,74)(H,63,73)(H,66,71)/b28-13-/t24-,32+,36-/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

Products are for research use only. Not for human use.