A 201A | CAS# 37305-78-5 | Antibiotic

MedKoo Cat#: 571079 | Name: A 201A

Description:

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

A 201A is a nucleoside antibiotic isolated from Streptomyces capreolus.

Chemical Structure

A 201A

CAS#37305-78-5

Theoretical Analysis

MedKoo Cat#: 571079

Name: A 201A

CAS#: 37305-78-5

Chemical Formula: C37H50N6O14

Exact Mass: 802.3385

Molecular Weight: 802.84

Elemental Analysis: C, 55.35; H, 6.28; N, 10.47; O, 27.90

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 #

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Synonym

A 201A; A201A; A-201A; Antibiotic 201A

IUPAC/Chemical Name

(E)-3-(4-(((Z)-3,4-dihydroxy-5-(2-((3-hydroxy-4,5-dimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-1-methoxyethylidene)tetrahydrofuran-2-yl)oxy)phenyl)-N-(5-(6-(dimethylamino)-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl)-2-methylacrylamide

InChi Key

HELPZWNRUYNCJQ-QWJSOBSRSA-N

InChi Code

InChI=1S/C37H50N6O14/c1-17(34(49)41-23-21(13-44)56-35(25(23)45)43-16-40-24-32(42(3)4)38-15-39-33(24)43)12-19-8-10-20(11-9-19)55-37-27(47)26(46)30(57-37)22(50-5)14-53-36-28(48)31(52-7)29(51-6)18(2)54-36/h8-12,15-16,18,21,23,25-29,31,35-37,44-48H,13-14H2,1-7H3,(H,41,49)/b17-12+,30-22-

SMILES Code

CC1C(OC)C(OC)C(O)C(OC/C(OC)=C2C(O)C(O)C(OC3=CC=C(/C=C(C(NC4C(CO)OC(N5C=NC6=C5N=CN=C6N(C)C)C4O)=O)\C)C=C3)O\2)O1

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 802.84 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: Nie S, Li W, Yu B. Total synthesis of nucleoside antibiotic A201A. J Am Chem Soc. 2014 Mar 19;136(11):4157-60. doi: 10.1021/ja501460j. Epub 2014 Mar 11. PubMed PMID: 24611434. 2: Nie S, Chen X, Ma Y, Li W, Yu B. An unexpected rearrangement of pent-4-enofuranosides to cyclopentanones upon hydrogenolysis of the anomeric benzyl group. Carbohydr Res. 2016 Sep 2;432:36-40. doi: 10.1016/j.carres.2016.06.006. Epub 2016 Jun 18. PubMed PMID: 27366975. 3: Kirst HA, Dorman DE, Occolowitz JL, Jones ND, Paschal JW, Hamill RL, Szymanski EF. The structure of A201A, a novel nucleoside antibiotic. J Antibiot (Tokyo). 1985 May;38(5):575-86. PubMed PMID: 4019309. 4: Zhu Q, Li J, Ma J, Luo M, Wang B, Huang H, Tian X, Li W, Zhang S, Zhang C, Ju J. Discovery and engineered overproduction of antimicrobial nucleoside antibiotic A201A from the deep-sea marine actinomycete Marinactinospora thermotolerans SCSIO 00652. Antimicrob Agents Chemother. 2012 Jan;56(1):110-4. doi: 10.1128/AAC.05278-11. Epub 2011 Nov 7. PubMed PMID: 22064543; PubMed Central PMCID: PMC3256081. 5: Barrasa MI, Tercero JA, Lacalle RA, Jimenez A. The ard1 gene from Streptomyces capreolus encodes a polypeptide of the ABC-transporters superfamily which confers resistance to the aminonucleoside antibiotic A201A. Eur J Biochem. 1995 Mar 15;228(3):562-9. PubMed PMID: 7737149. 6: Barrasa MI, Tercero JA, Jimenez A. The aminonucleoside antibiotic A201A is inactivated by a phosphotransferase activity from Streptomyces capreolus NRRL 3817, the producing organism. Isolation and molecular characterization of the relevant encoding gene and its DNA flanking regions. Eur J Biochem. 1997 Apr 1;245(1):54-63. PubMed PMID: 9128724. 7: Saugar I, Molloy B, Sanz E, Blanca Sánchez M, Fernández-Lobato M, Jiménez A. Characterization of the biosynthetic gene cluster (ata) for the A201A aminonucleoside antibiotic from Saccharothrix mutabilis subsp. capreolus. J Antibiot (Tokyo). 2017 Apr;70(4):404-413. doi: 10.1038/ja.2016.123. Epub 2016 Oct 12. PubMed PMID: 27731336. 8: Polikanov YS, Starosta AL, Juette MF, Altman RB, Terry DS, Lu W, Burnett BJ, Dinos G, Reynolds KA, Blanchard SC, Steitz TA, Wilson DN. Distinct tRNA Accommodation Intermediates Observed on the Ribosome with the Antibiotics Hygromycin A and A201A. Mol Cell. 2015 Jun 4;58(5):832-44. doi: 10.1016/j.molcel.2015.04.014. Epub 2015 May 28. PubMed PMID: 26028538; PubMed Central PMCID: PMC4458074. 9: Coutard B, Barral K, Lichière J, Selisko B, Martin B, Aouadi W, Lombardia MO, Debart F, Vasseur JJ, Guillemot JC, Canard B, Decroly E. Zika Virus Methyltransferase: Structure and Functions for Drug Design Perspectives. J Virol. 2017 Feb 14;91(5). pii: e02202-16. doi: 10.1128/JVI.02202-16. Print 2017 Mar 1. PubMed PMID: 28031359; PubMed Central PMCID: PMC5309936.