Telomycin | CAS# 19246-24-3 | Antibiotic

MedKoo Cat#: 571017 | Name: Telomycin

Description:

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

Telomycin is a cyclic depsipeptide antibiotic active against Gram-positive bacteria. It is a rapid agent against bacteria, including multidrug-resistant (MDR) Gram-positive pathogens. Biosynthetic pathways of telomycin and related semisynthetic lipopeptide antibiotic derivatives are being studied for future chemical optimization for pharmaceutical application.

Chemical Structure

Telomycin

CAS#19246-24-3

Theoretical Analysis

MedKoo Cat#: 571017

Name: Telomycin

CAS#: 19246-24-3

Chemical Formula: C59H77N13O19

Exact Mass: 1271.5459

Molecular Weight: 1272.34

Elemental Analysis: C, 55.70; H, 6.10; N, 14.31; O, 23.89

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Telomycin, A-128, A 128, A128, Antibiotic 128, NSC 235069

IUPAC/Chemical Name

N4-((2S)-1-(((1S,9S,12S,15S,16R,18aS,19R,24S,27S,32aS,E)-27-(1-(1H-indol-3-yl)ethyl)-30-((1H-indol-3-yl)methylene)-1,19-dihydroxy-24-((S)-1-hydroxy-2-methylpropyl)-12-((S)-1-hydroxyethyl)-9,16-dimethyl-5,8,11,14,18,23,26,29,32-nonaoxotriacontahydro-18H-dipyrrolo[2,1-c:2',1'-o][1]oxa[4,7,10,13,16,19,22,25]octaazacyclooctacosin-15-yl)amino)-3-hydroxy-1-oxopropan-2-yl)-L-asparagine

InChi Key

FJEKCPBQVANMTA-GRZFNQFESA-N

InChi Code

1S/C59H77N13O19/c1-25(2)49(79)46-57(87)72-18-16-40(76)48(72)59(90)91-29(6)45(69-52(82)38(24-73)65-41(77)20-34(60)58(88)89)55(85)68-44(28(5)74)54(84)64-27(4)50(80)63-23-42(78)71-17-15-39(75)47(71)56(86)66-37(19-30-21-61-35-13-9-7-11-31(30)35)51(81)67-43(53(83)70-46)26(3)33-22-62-36-14-10-8-12-32(33)36/h7-14,19,21-22,25-29,34,38-40,43-49,61-62,73-76,79H,15-18,20,23-24,60H2,1-6H3,(H,63,80)(H,64,84)(H,65,77)(H,66,86)(H,67,81)(H,68,85)(H,69,82)(H,70,83)(H,88,89)/t26?,27-,28-,29+,34-,38-,39-,40+,43-,44-,45-,46-,47-,48-,49-/m0/s1

SMILES Code

CC([C@@H]([C@@H]1NC([C@H](C(c(c[nH]2)c3c2cccc3)C)NC(/C(NC([C@@H]4[C@H](CCN4C(CNC([C@@H](NC([C@H]([C@@H](O)C)NC([C@H]([C@H](OC([C@@H]5[C@@H](CCN5C1=O)O)=O)C)NC([C@@H](NC(C[C@@H](C(O)=O)N)=O)CO)=O)=O)=O)C)=O)=O)O)=O)=C\c(c[nH]6)c7c6cccc7)=O)=O)O)C

Appearance

Solid powder

Purity

>98% (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 1,272.34 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: Wei S, Zhang W, Ji Z. Structure and Antibacterial Activity of Ambobactin, a New Telomycin-Like Cyclic Depsipeptide Antibiotic Produced by Streptomyces ambofaciens F3. Molecules. 2015 Sep 9;20(9):16278-89. doi: 10.3390/molecules200916278. PubMed PMID: 26370952. 2: Vela Gurovic MS, Müller S, Domin N, Seccareccia I, Nietzsche S, Martin K, Nett M. Micromonospora schwarzwaldensis sp. nov., a producer of telomycin, isolated from soil. Int J Syst Evol Microbiol. 2013 Oct;63(Pt 10):3812-7. doi: 10.1099/ijs.0.051623-0. Epub 2013 May 10. PubMed PMID: 23667141. 3: Fu C, Keller L, Bauer A, Brönstrup M, Froidbise A, Hammann P, Herrmann J, Mondesert G, Kurz M, Schiell M, Schummer D, Toti L, Wink J, Müller R. Biosynthetic Studies of Telomycin Reveal New Lipopeptides with Enhanced Activity. J Am Chem Soc. 2015 Jun 24;137(24):7692-705. doi: 10.1021/jacs.5b01794. Epub 2015 Jun 15. PubMed PMID: 26043159. 4: MISIEK M, FARDIG OB, GOUREVITCH A, JOHNSON DL, HOOPER IR, LEIN J. Telomycin, a new antibiotic. Antibiot Annu. 1957-1958;5:852-5. PubMed PMID: 13521903. 5: TISCH DE, HUFTALEN JB, DICKISON HL. Pharmacological studies with telomycin. Antibiot Annu. 1957-1958;5:863-8. PubMed PMID: 13521905. 6: GOUREVITCH A, HUNT GA, MOSES AJ, ZANGARI V, PUGLISI T, LEIN J. Microbiological studies on telomycin. Antibiot Annu. 1957-1958;5:856-62. PubMed PMID: 13521904. 7: Sheehan JC, Mania D, Nakamura S, Stock JA, Maeda K. The structure of telomycin. J Am Chem Soc. 1968 Jan 17;90(2):462-70. PubMed PMID: 5634622. 8: Johnston CW, Skinnider MA, Dejong CA, Rees PN, Chen GM, Walker CG, French S, Brown ED, Bérdy J, Liu DY, Magarvey NA. Assembly and clustering of natural antibiotics guides target identification. Nat Chem Biol. 2016 Apr;12(4):233-9. doi: 10.1038/nchembio.2018. Epub 2016 Feb 1. PubMed PMID: 26829473. 9: Kumar NG, Urry DW. Proton magnetic resonance assignments of the polypeptide antibiotic telomycin. Biochemistry. 1973 Sep 25;12(20):3811-7. PubMed PMID: 4745647. 10: Kumar NG, Urry DW. Conformational analysis of the polypeptide antibiotic telomycin by nuclear magnetic resonance. Biochemistry. 1973 Oct 23;12(22):4392-9. PubMed PMID: 4750250. 11: IRREVERRE F, MORITA K, ISHII S, WITKOP B. Occurrence of cis- and trans-3-hydroxy-L-proline in acid hydrolyzate of telomycin. Biochem Biophys Res Commun. 1962 Sep 25;9:69-71. PubMed PMID: 13956698. 12: Liu DY, Li Y, Magarvey NA. Draft Genome Sequence of Streptomyces canus ATCC 12647, a Producer of Telomycin. Genome Announc. 2016 Mar 24;4(2). pii: e00173-16. doi: 10.1128/genomeA.00173-16. PubMed PMID: 27013049; PubMed Central PMCID: PMC4807238. 13: Irreverre F. Amino acid composition of telomycin-producing streptomyces. Biochim Biophys Acta. 1966 Apr 25;117(2):485-6. PubMed PMID: 5961312. 14: PACKCHANIAN A. Chemotherapy of Borrelia anserina infection (spirochetosis) in chicks with amphomycin, kanamycin. telomycin. and tetracycline. Antibiot Chemother (Northfield). 1960 Dec;10:731-9. PubMed PMID: 13731948. 15: Oliva B, Maiese WM, Greenstein M, Borders DB, Chopra I. Mode of action of the cyclic depsipeptide antibiotic LL-AO341 beta 1 and partial characterization of a Staphylococcus aureus mutant resistant to the antibiotic. J Antimicrob Chemother. 1993 Dec;32(6):817-30. PubMed PMID: 7511579. 16: Mori H, Shibasaki T, Uozaki Y, Ochiai K, Ozaki A. Detection of Novel Proline 3-Hydroxylase Activities in Streptomyces and Bacillus spp. by Regio- and Stereospecific Hydroxylation of l-Proline. Appl Environ Microbiol. 1996 Jun;62(6):1903-7. PubMed PMID: 16535329; PubMed Central PMCID: PMC1388867.