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MedKoo Cat#: 596909 | Name: Aspergillomarasmine A

Description:

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

Aspergillomarasmine A is a polyamino acid naturally produced by the mold Aspergillus versicolor. The substance has been reported to inhibit two antibiotic resistance carbapenemase proteins in bacteria, New Delhi metallo-beta-lactamase 1 (NDM-1) and Verona integron-encoded metallo-beta-lactamase (VIM-2), and make those antibiotic-resistant bacteria susceptible to antibiotics. Aspergillomarasmine A is toxic to leaves of barley and other plants, being termed as "Toxin C" when produced by Pyrenophora teres.

Chemical Structure

Aspergillomarasmine A
Aspergillomarasmine A
CAS#3484-65-9

Theoretical Analysis

MedKoo Cat#: 596909

Name: Aspergillomarasmine A

CAS#: 3484-65-9

Chemical Formula: C10H17N3O8

Exact Mass: 307.1016

Molecular Weight: 307.25

Elemental Analysis: C, 39.09; H, 5.58; N, 13.68; O, 41.66

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
Aspergillomarasmine A; Toxin C (Pyrenophora teres);
IUPAC/Chemical Name
L-Aspartic acid, N-(2-((2-amino-2-carboxyethyl)amino)-2-carboxyethyl)-, (R-(R*,R*))-
InChi Key
O=C(O)C[C@@H](C(O)=O)NC[C@@H](NC[C@@H](N)C(O)=O)C(O)=O
InChi Code
InChI=1S/C10H17N3O8/c11-4(8(16)17)2-12-6(10(20)21)3-13-5(9(18)19)1-7(14)15/h4-6,12-13H,1-3,11H2,(H,14,15)(H,16,17)(H,18,19)(H,20,21)/t4-,5+,6-/m1/s1
SMILES Code
O=C(O)C[C@@H](C(O)=O)NC[C@@H](NC[C@@H](N)C(O)=O)C(O)=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 307.25 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.

Recalculate based on batch purity %
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: Zhang J, Wang S, Bai Y, Guo Q, Zhou J, Lei X. Total Syntheses of Natural Metallophores Staphylopine and Aspergillomarasmine A. J Org Chem. 2017 Dec 15;82(24):13643-13648. doi: 10.1021/acs.joc.7b02342. Epub 2017 Nov 30. PubMed PMID: 29115130. 2: Bergstrom A, Katko A, Adkins Z, Hill J, Cheng Z, Burnett M, Yang H, Aitha M, Mehaffey MR, Brodbelt JS, Tehrani KHME, Martin NI, Bonomo RA, Page RC, Tierney DL, Fast W, Wright GD, Crowder MW. Probing the Interaction of Aspergillomarasmine A with Metallo-β-lactamases NDM-1, VIM-2, and IMP-7. ACS Infect Dis. 2018 Feb 9;4(2):135-145. doi: 10.1021/acsinfecdis.7b00106. Epub 2017 Nov 9. PubMed PMID: 29091730; PubMed Central PMCID: PMC5807211. 3: Zhang J, Wang S, Wei Q, Guo Q, Bai Y, Yang S, Song F, Zhang L, Lei X. Synthesis and biological evaluation of Aspergillomarasmine A derivatives as novel NDM-1 inhibitor to overcome antibiotics resistance. Bioorg Med Chem. 2017 Oct 1;25(19):5133-5141. doi: 10.1016/j.bmc.2017.07.025. Epub 2017 Jul 14. PubMed PMID: 28784300. 4: Dolgin E. Inner Workings: Combating antibiotic resistance from the ground up. Proc Natl Acad Sci U S A. 2016 Oct 18;113(42):11642-11643. PubMed PMID: 27791044; PubMed Central PMCID: PMC5081612. 5: Albu SA, Koteva K, King AM, Al-Karmi S, Wright GD, Capretta A. Total Synthesis of Aspergillomarasmine A and Related Compounds: A Sulfamidate Approach Enables Exploration of Structure-Activity Relationships. Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13259-13262. doi: 10.1002/anie.201606657. PubMed PMID: 27633338. 6: Koteva K, King AM, Capretta A, Wright GD. Total Synthesis and Activity of the Metallo-β-lactamase Inhibitor Aspergillomarasmine A. Angew Chem Int Ed Engl. 2016 Feb 5;55(6):2210-2. doi: 10.1002/anie.201510057. Epub 2015 Dec 28. PubMed PMID: 26709849. 7: Liao D, Yang S, Wang J, Zhang J, Hong B, Wu F, Lei X. Total Synthesis and Structural Reassignment of Aspergillomarasmine A. Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4291-5. doi: 10.1002/anie.201509960. Epub 2015 Nov 23. PubMed PMID: 26592805. 8: von Nussbaum F, Schiffer G. Aspergillomarasmine A, an inhibitor of bacterial metallo-β-lactamases conferring blaNDM and blaVIM resistance. Angew Chem Int Ed Engl. 2014 Oct 27;53(44):11696-8. doi: 10.1002/anie.201407921. Epub 2014 Sep 24. PubMed PMID: 25256630. 9: King AM, Reid-Yu SA, Wang W, King DT, De Pascale G, Strynadka NC, Walsh TR, Coombes BK, Wright GD. Aspergillomarasmine A overcomes metallo-β-lactamase antibiotic resistance. Nature. 2014 Jun 26;510(7506):503-6. doi: 10.1038/nature13445. PubMed PMID: 24965651; PubMed Central PMCID: PMC4981499. 10: Meziane-Cherif D, Courvalin P. Antibiotic resistance: to the rescue of old drugs. Nature. 2014 Jun 26;510(7506):477-8. doi: 10.1038/510477a. PubMed PMID: 24965645. 11: Matsuura A, Okumura H, Asakura R, Ashizawa N, Takahashi M, Kobayashi F, Ashikawa N, Arai K. Pharmacological profiles of aspergillomarasmines as endothelin converting enzyme inhibitors. Jpn J Pharmacol. 1993 Oct;63(2):187-93. PubMed PMID: 8283829. 12: Friis P, Olsen CE, Møller BL. Toxin production in Pyrenophora teres, the ascomycete causing the net-spot blotch disease of barley (Hordeum vulgare L.). J Biol Chem. 1991 Jul 15;266(20):13329-35. PubMed PMID: 2071605. 13: Trouvelot A, Camporota P, Barbier M, Pouteau-Thouvenot M. [Isolation of aspergillomarasmine A from the culture media of Fusarium oxysporum f. sp. melonia]. C R Acad Sci Hebd Seances Acad Sci D. 1971 Feb 1;272(5):754-6. French. PubMed PMID: 4995047.