Tirandamycin A | CAS#34429-70-4

MedKoo Cat#: 462810 | Name: Tirandamycin A

Description:

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

Tirandamycin A is an antibiotic related to streptolydigin.

Chemical Structure

Tirandamycin A

CAS#34429-70-4

Theoretical Analysis

MedKoo Cat#: 462810

Name: Tirandamycin A

CAS#: 34429-70-4

Chemical Formula: C22H27NO7

Exact Mass: 417.1788

Molecular Weight: 417.46

Elemental Analysis: C, 63.30; H, 6.52; N, 3.36; O, 26.83

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

NSC 107067; NSC-107067; NSC107067;

IUPAC/Chemical Name

(E)-3-((R,2E,4E)-1-hydroxy-4-methyl-6-((1R,2S,4R,6R,7R,8R)-1,2,7-trimethyl-5-oxo-3,9,10-trioxatricyclo[4.3.1.02,4]decan-8-yl)hepta-2,4-dien-1-ylidene)pyrrolidine-2,4-dione

InChi Key

URGUBECARCAPRI-UYXUTHQNSA-N

InChi Code

InChI=1S/C22H27NO7/c1-10(6-7-13(24)15-14(25)9-23-20(15)27)8-11(2)17-12(3)18-16(26)19-21(4,30-19)22(5,28-17)29-18/h6-8,11-12,17-19,24H,9H2,1-5H3,(H,23,27)/b7-6+,10-8+,15-13+/t11-,12-,17-,18-,19+,21+,22-/m1/s1

SMILES Code

C[C@@H]([C@H]1O[C@@]2(O[C@@H](C([C@@H]3O[C@]23C)=O)[C@@H]1C)C)/C=C(/C=C/C(O)=C4C(CNC/4=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

>3 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 417.46 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: Mo X, Huang H, Ma J, Wang Z, Wang B, Zhang S, Zhang C, Ju J. Characterization of TrdL as a 10-hydroxy dehydrogenase and generation of new analogues from a tirandamycin biosynthetic pathway. Org Lett. 2011 May 6;13(9):2212-5. doi: 10.1021/ol200447h. Epub 2011 Apr 1. PMID: 21456513. 2: Espinosa A, Socha AM, Ryke E, Rowley DC. Antiamoebic properties of the actinomycete metabolites echinomycin A and tirandamycin A. Parasitol Res. 2012 Dec;111(6):2473-7. doi: 10.1007/s00436-012-3019-2. Epub 2012 Jul 5. PMID: 22763704; PMCID: PMC3491104. 3: Mo X, Ma J, Huang H, Wang B, Song Y, Zhang S, Zhang C, Ju J. Δ(11,12) double bond formation in tirandamycin biosynthesis is atypically catalyzed by TrdE, a glycoside hydrolase family enzyme. J Am Chem Soc. 2012 Feb 15;134(6):2844-7. doi: 10.1021/ja206713a. Epub 2012 Feb 1. PMID: 22280373. 4: Carlson JC, Fortman JL, Anzai Y, Li S, Burr DA, Sherman DH. Identification of the tirandamycin biosynthetic gene cluster from Streptomyces sp. 307-9. Chembiochem. 2010 Mar 1;11(4):564-72. doi: 10.1002/cbic.200900658. PMID: 20127927; PMCID: PMC3019614. 5: Carlson JC, Li S, Gunatilleke SS, Anzai Y, Burr DA, Podust LM, Sherman DH. Tirandamycin biosynthesis is mediated by co-dependent oxidative enzymes. Nat Chem. 2011 Jul 17;3(8):628-33. doi: 10.1038/nchem.1087. PMID: 21778983; PMCID: PMC3154026. 6: Zhen X, Gong T, Liu F, Zhang PC, Zhou WQ, Li Y, Zhu P. A New Analogue of Echinomycin and a New Cyclic Dipeptide from a Marine-Derived Streptomyces sp. LS298. Mar Drugs. 2015 Nov 18;13(11):6947-61. doi: 10.3390/md13116947. PMID: 26593927; PMCID: PMC4663560. 7: Karwowski JP, Jackson M, Theriault RJ, Barlow GJ, Coen L, Hensey DM, Humphrey PE. Tirandalydigin, a novel tetramic acid of the tirandamycin-streptolydigin type. I. Taxonomy of the producing organism, fermentation and biological activity. J Antibiot (Tokyo). 1992 Jul;45(7):1125-32. doi: 10.7164/antibiotics.45.1125. PMID: 1517158. 8: Hagenmaier H, Jaschke KH, Santo L, Scheer M, Zähner H. Stoffwechselprodukte von Mikroorganismen. 158. Mitteilung. Tirandamycin B [Metabiolic products of microorganisms. Tirandamycin B(author's transl)]. Arch Microbiol. 1976 Aug;109(1-2):65-74. German. doi: 10.1007/BF00425114. PMID: 962473. 9: Parvez M, Lin MT, DeShong P. (2S-[2 alpha,3 alpha,3a beta,6 beta(R*),7 alpha, 7a alpha])-6-(3-benzyloxy-2-propyl)-2-hydroxy-2,3,7-trimethylhexahydro-4H- furo [3,2-c]pyran-4-one, a rearrangement product of pyranone derivatives in the tirandamycin A series. Acta Crystallogr C. 1992 Oct 15;48 ( Pt 10):1906-8. doi: 10.1107/s0108270192005754. PMID: 1445676. 10: Reusser F. Tirandamycin, an inhibitor of bacterial ribonucleic acid polymerase. Antimicrob Agents Chemother. 1976 Oct;10(4):618-22. doi: 10.1128/aac.10.4.618. PMID: 791108; PMCID: PMC429803. 11: Meyer CE. Tirandamycin, a new antibiotic isolation and characterization. J Antibiot (Tokyo). 1971 Aug;24(8):558-60. doi: 10.7164/antibiotics.24.558. PMID: 5092790. 12: Hatakeyama S. [Stereocontrolled Total Synthesis of Biologically Active Natural Products]. Yakugaku Zasshi. 2018;138(2):191-209. Japanese. doi: 10.1248/yakushi.17-00187. PMID: 29386433. 13: Lee VJ, Rinehart KL Jr. C NMR spectra of streptolydigin, tirandamycin, and related degradation products. J Antibiot (Tokyo). 1980 Apr;33(4):408-15. doi: 10.7164/antibiotics.33.408. PMID: 6902724. 14: Rosen T, Fernandes PB, Marovich MA, Shen L, Mao J, Pernet AG. Aromatic dienoyl tetramic acids. Novel antibacterial agents with activity against anaerobes and staphylococci. J Med Chem. 1989 May;32(5):1062-9. doi: 10.1021/jm00125a022. PMID: 2709374. 15: Yoshimura H, Takahashi K, Ishihara J, Hatakeyama S. Unified synthesis of tirandamycins and streptolydigins. Chem Commun (Camb). 2015 Dec 11;51(95):17004-7. doi: 10.1039/c5cc07749d. PMID: 26448062. 16: Ogasawara Y, Kondo K, Ikeda A, Harada R, Dairi T. Identification of tirandamycins as specific inhibitors of the futalosine pathway. J Antibiot (Tokyo). 2017 Jun;70(6):798-800. doi: 10.1038/ja.2017.22. Epub 2017 Mar 1. PMID: 28246380.

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