A 201A

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

MedKoo CAT#: 571079

CAS#: 37305-78-5

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


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A 201A is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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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


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


Technical Data

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).

Harmonized System Code:
293490


References

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.