Bottromycin A2 | CAS#15005-62-6 | Streptomyces antibiotic

MedKoo Cat#: 463971 | Name: Bottromycin A2

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bottromycin A2 is an antibiotic originally isolated from Streptomyces. It blocks the binding of aminoacyl-tRNA to the A site of the 50S ribosome, inhibiting protein synthesis. Bottromycin A2 is active against clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci with MIC values of 1 and 0.5 µg/ml, respectively.

Chemical Structure

Bottromycin A2

CAS#15005-62-6

Theoretical Analysis

MedKoo Cat#: 463971

Name: Bottromycin A2

CAS#: 15005-62-6

Chemical Formula: C42H62N8O7S

Exact Mass: 822.4462

Molecular Weight: 823.07

Elemental Analysis: C, 61.29; H, 7.59; N, 13.61; O, 13.61; S, 3.90

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Synonym

Bottromycin A2; Bottromycin-A2;

IUPAC/Chemical Name

methyl (R)-3-((2S,3S)-2-((S)-2-(((3S,6S,14R,14aS,E)-6-(tert-butyl)-3-isopropyl-14-methyl-1,4,10-trioxo-1,2,3,4,5,6,9,10,12,13,14,14a-dodecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecin-7-yl)amino)-3,3-dimethylbutanamido)-3-phenylbutanamido)-3-(thiazol-2-yl)propanoate

InChi Key

KSIZLOPUXFSFNR-XZNJZDOZSA-N

InChi Code

InChI=1S/C42H62N8O7S/c1-23(2)30-36(53)49-33(41(5,6)7)35(44-22-28(51)50-19-17-24(3)32(50)38(55)46-30)48-34(42(8,9)10)39(56)47-31(25(4)26-15-13-12-14-16-26)37(54)45-27(21-29(52)57-11)40-43-18-20-58-40/h12-16,18,20,23-25,27,30-34H,17,19,21-22H2,1-11H3,(H,44,48)(H,45,54)(H,46,55)(H,47,56)(H,49,53)/t24-,25+,27-,30+,31+,32+,33-,34-/m1/s1

SMILES Code

O=C1[C@]2(N(C(C/N=C(N[C@H](C(N[C@@H]([C@@H](C)C3=CC=CC=C3)C(N[C@H](CC(OC)=O)C4=NC=CS4)=O)=O)C(C)(C)C)\[C@H](C(C)(C)C)NC([C@H](C(C)C)N1)=O)=O)CC[C@H]2C)[H]

Appearance

Solid powder

Purity

>80% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 823.07 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Arn F, Frasson D, Kroslakova I, Rezzonico F, Pothier JF, Riedl R, Sievers M. Isolation and Identification of Actinomycetes Strains from Switzerland and their Biotechnological Potential. Chimia (Aarau). 2020 May 27;74(5):382-390. doi: 10.2533/chimia.2020.382. PMID: 32482215. 2: Sikandar A, Franz L, Melse O, Antes I, Koehnke J. Thiazoline-Specific Amidohydrolase PurAH Is the Gatekeeper of Bottromycin Biosynthesis. J Am Chem Soc. 2019 Jun 26;141(25):9748-9752. doi: 10.1021/jacs.8b12231. Epub 2019 Jun 13. PMID: 31192589. 3: Yamada T, Yagita M, Kobayashi Y, Sennari G, Shimamura H, Matsui H, Horimatsu Y, Hanaki H, Hirose T, O Mura S, Sunazuka T. Synthesis and Evaluation of Antibacterial Activity of Bottromycins. J Org Chem. 2018 Jul 6;83(13):7135-7149. doi: 10.1021/acs.joc.8b00045. Epub 2018 Apr 16. PMID: 29560726. 4: Yin M, Jiang M, Ren Z, Dong Y, Lu T. The complete genome sequence of Streptomyces autolyticus CGMCC 0516, the producer of geldanamycin, autolytimycin, reblastatin and elaiophylin. J Biotechnol. 2017 Jun 20;252:27-31. doi: 10.1016/j.jbiotec.2017.04.037. Epub 2017 May 2. PMID: 28472671. 5: Crone WJ, Vior NM, Santos-Aberturas J, Schmitz LG, Leeper FJ, Truman AW. Dissecting Bottromycin Biosynthesis Using Comparative Untargeted Metabolomics. Angew Chem Int Ed Engl. 2016 Aug 8;55(33):9639-43. doi: 10.1002/anie.201604304. Epub 2016 Jul 4. PMID: 27374993; PMCID: PMC5103208. 6: Gouda H, Kobayashi Y, Yamada T, Ideguchi T, Sugawara A, Hirose T, Omura S, Sunazuka T, Hirono S. Three-dimensional solution structure of bottromycin A2: a potent antibiotic active against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococci. Chem Pharm Bull (Tokyo). 2012;60(2):169-71. doi: 10.1248/cpb.60.169. PMID: 22293474. 7: Park SB, Lee IA, Suh JW, Kim JG, Lee CH. Screening and identification of antimicrobial compounds from Streptomyces bottropensis suppressing rice bacterial blight. J Microbiol Biotechnol. 2011 Dec;21(12):1236-42. doi: 10.4014/jmb.1106.06047. PMID: 22210608. 8: Kobayashi Y, Ichioka M, Hirose T, Nagai K, Matsumoto A, Matsui H, Hanaki H, Masuma R, Takahashi Y, Omura S, Sunazuka T. Bottromycin derivatives: efficient chemical modifications of the ester moiety and evaluation of anti-MRSA and anti- VRE activities. Bioorg Med Chem Lett. 2010 Oct 15;20(20):6116-20. doi: 10.1016/j.bmcl.2010.08.037. Epub 2010 Aug 18. PMID: 20833545. 9: Shimamura H, Gouda H, Nagai K, Hirose T, Ichioka M, Furuya Y, Kobayashi Y, Hirono S, Sunazuka T, Omura S. Structure determination and total synthesis of bottromycin A2: a potent antibiotic against MRSA and VRE. Angew Chem Int Ed Engl. 2009;48(5):914-7. doi: 10.1002/anie.200804138. PMID: 19115340. 10: Kaneda M. Studies on bottromycins. I. 1H and 13C NMR assignments of bottromycin A2, the main component of the complex. J Antibiot (Tokyo). 1992 May;45(5):792-6. doi: 10.7164/antibiotics.45.792. PMID: 1624382. 11: Sowa S, Masumi N, Inouye Y, Nakamura S, Takesue Y, Yokoyama T. Susceptibility of methicillin-resistant Staphylococcus aureus clinical isolates to various antimicrobial agents. Hiroshima J Med Sci. 1991 Dec;40(4):137-44. PMID: 1797744. 12: Singh SK, Gurusiddaiah S. Production, purification, and characterization of chandramycin, a polypeptide antibiotic from Streptomyces lydicus. Antimicrob Agents Chemother. 1984 Sep;26(3):394-400. doi: 10.1128/aac.26.3.394. PMID: 6548890; PMCID: PMC176177. 13: Schipper D. The revised structure of bottromycin A2. J Antibiot (Tokyo). 1983 Aug;36(8):1076-7. doi: 10.7164/antibiotics.36.1076. PMID: 6630058. 14: Otaka T, Kaji A. Mode of action of bottromycin A2: effect of bottromycin A2 on polysomes. FEBS Lett. 1983 Mar 7;153(1):53-9. doi: 10.1016/0014-5793(83)80118-5. PMID: 6337880. 15: Otaka T, Kaji A. Mode of action of bottromycin A2: effect on peptide bond formation. FEBS Lett. 1981 Jan 26;123(2):173-6. doi: 10.1016/0014-5793(81)80280-3. PMID: 7014241. 16: Liao YL. Studies on the new cell line TT-I: viral susceptibility and chromosomal changes related to mycoplasma contamination. Zhonghua Min Guo Wei Sheng Wu Xue Za Zhi. 1976 Dec;9(3-4):37-44. PMID: 1037533. 17: Takahashi Y, Naganawa H, Takita T, Umezawa H, Nakamura S. The revised structure of bottromycin A2. J Antibiot (Tokyo). 1976 Oct;29(10):1120-3. doi: 10.7164/antibiotics.29.1120. PMID: 994331. 18: Otaka T, Kaji A. Mode of action of bottromycin A2. Release of aminoacyl- or peptidyl-tRNA from ribosomes. J Biol Chem. 1976 Apr 25;251(8):2299-306. PMID: 770464. 19: Kinoshita T, Tanaka N. On the site of action of bottromycin A2. J Antibiot (Tokyo). 1970 Jun;23(6):311-2. doi: 10.7164/antibiotics.23.311. PMID: 5458308. 20: Lin YC, Kinoshita T, Tanak N. Mechanism of protein synthesis inhibition by bottromycin A2: studies with puromycin. J Antibiot (Tokyo). 1968 Aug;21(8):471-6. doi: 10.7164/antibiotics.21.471. PMID: 4884807.