MedKoo Cat#: 208417 | Name: Mycosidine

Description:

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

Mycosidine is a novel antifungal agent

Chemical Structure

Mycosidine
Mycosidine
CAS#181465-11-2

Theoretical Analysis

MedKoo Cat#: 208417

Name: Mycosidine

CAS#: 181465-11-2

Chemical Formula: C12H8ClNO4S

Exact Mass: 296.9863

Molecular Weight: 297.71

Elemental Analysis: C, 48.41; H, 2.71; Cl, 11.91; N, 4.70; O, 21.50; S, 10.77

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
IUPAC/Chemical Name
Methyl (Z)-5-(4-chlorobenzylidene)-2,4-dioxothiazolidine-3-carboxylate
InChi Key
NHCQXGMKPONWTA-TWGQIWQCSA-N
InChi Code
InChI=1S/C12H8ClNO4S/c1-18-11(16)14-10(15)9(19-12(14)17)6-7-2-4-8(13)5-3-7/h2-6H,1H3/b9-6-
SMILES Code
O=C(N(C/1=O)C(SC1=C/C2=CC=C(Cl)C=C2)=O)OC
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 297.71 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: Borowski E, Salewska N, Boros-Majewska J, Serocki M, Chabowska I, Milewska MJ, Ziętkowski D, Milewski S. The Substantial Improvement of Amphotericin B Selective Toxicity Upon Modification of Mycosamine with Bulky Substituents. Med Chem. 2020;16(1):128-139. doi: 10.2174/1573406415666181203114629. PMID: 30501601. 2: Alais J, David S. A precursor to the beta-pyranosides of 3-amino-3,6-dideoxy- D-mannose (mycosamine). Carbohydr Res. 1992 Jun 4;230(1):79-87. doi: 10.1016/s0008-6215(00)90514-7. PMID: 1511455. 3: Nedal A, Sletta H, Brautaset T, Borgos SE, Sekurova ON, Ellingsen TE, Zotchev SB. Analysis of the mycosamine biosynthesis and attachment genes in the nystatin biosynthetic gene cluster of Streptomyces noursei ATCC 11455. Appl Environ Microbiol. 2007 Nov;73(22):7400-7. doi: 10.1128/AEM.01122-07. Epub 2007 Sep 28. PMID: 17905880; PMCID: PMC2168226. 4: Paquet V, Carreira EM. Significant improvement of antifungal activity of polyene macrolides by bisalkylation of the mycosamine. Org Lett. 2006 Apr 27;8(9):1807-9. doi: 10.1021/ol060353o. PMID: 16623556. 5: Matsumori N, Sawada Y, Murata M. Mycosamine orientation of amphotericin B controlling interaction with ergosterol: sterol-dependent activity of conformation-restricted derivatives with an amino-carbonyl bridge. J Am Chem Soc. 2005 Aug 3;127(30):10667-75. doi: 10.1021/ja051597r. PMID: 16045354. 6: Croatt MP, Carreira EM. Probing the role of the mycosamine C2'-OH on the activity of amphotericin B. Org Lett. 2011 Mar 18;13(6):1390-3. doi: 10.1021/ol2000765. Epub 2011 Feb 15. PMID: 21322610. 7: Volmer AA, Carreira EM. Active amphotericin B derivatives position the mycosamine in two radial orientations. Chembiochem. 2010 Apr 12;11(6):778-81. doi: 10.1002/cbic.201000080. PMID: 20217884. 8: Packard GK, Rychnovsky SD. Beta-selective glycosylations with masked D-mycosamine precursors. Org Lett. 2001 Oct 18;3(21):3393-6. doi: 10.1021/ol016617i. PMID: 11594842. 9: Walmsley S, De Poire E, Rawlings B, Caffrey P. Engineered biosynthesis and characterisation of disaccharide-modified 8-deoxyamphoteronolides. Appl Microbiol Biotechnol. 2017 Mar;101(5):1899-1905. doi: 10.1007/s00253-016-7986-6. Epub 2016 Nov 17. PMID: 27858138. 10: Caffrey P, De Poire E, Sheehan J, Sweeney P. Polyene macrolide biosynthesis in streptomycetes and related bacteria: recent advances from genome sequencing and experimental studies. Appl Microbiol Biotechnol. 2016 May;100(9):3893-908. doi: 10.1007/s00253-016-7474-z. Epub 2016 Mar 29. PMID: 27023916.