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MedKoo Cat#: 463013 | Name: Amipurimycin

Description:

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

Amipurimycin a member of the complex peptidyl nucleoside family of antibiotics. It is a Streptomyces-derived potent antifungal agent.

Chemical Structure

Amipurimycin
Amipurimycin
CAS#61991-08-0

Theoretical Analysis

MedKoo Cat#: 463013

Name: Amipurimycin

CAS#: 61991-08-0

Chemical Formula: C20H29N7O8

Exact Mass: 495.2078

Molecular Weight: 495.49

Elemental Analysis: C, 48.48; H, 5.90; N, 19.79; O, 25.83

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 #
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Synonym
Amipurimycin;
IUPAC/Chemical Name
2-(6-(2-amino-9H-purin-9-yl)-4-(1,2-dihydroxyethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)-2-(2-aminocyclopentane-1-carboxamido)acetic acid
InChi Key
BHAUQSKSOITMND-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H29N7O8/c21-9-3-1-2-8(9)16(31)25-13(18(32)33)11-4-20(34,12(29)6-28)14(30)17(35-11)27-7-24-10-5-23-19(22)26-15(10)27/h5,7-9,11-14,17,28-30,34H,1-4,6,21H2,(H,25,31)(H,32,33)(H2,22,23,26)
SMILES Code
NC1CCCC1C(NC(C(O)=O)C2CC(C(CO)O)(C(C(n(cn3)c4c3cnc(N)n4)O2)O)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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 495.49 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: Wang S, Zhang Q, Zhao Y, Sun J, Kang W, Wang F, Pan H, Tang G, Yu B. The Miharamycins and Amipurimycin: their Structural Revision and the Total Synthesis of the Latter. Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10558-10562. doi: 10.1002/anie.201905723. Epub 2019 Jul 1. PMID: 31190371. 2: Romo AJ, Shiraishi T, Ikeuchi H, Lin GM, Geng Y, Lee YH, Liem PH, Ma T, Ogasawara Y, Shin-Ya K, Nishiyama M, Kuzuyama T, Liu HW. The Amipurimycin and Miharamycin Biosynthetic Gene Clusters: Unraveling the Origins of 2-Aminopurinyl Peptidyl Nucleoside Antibiotics. J Am Chem Soc. 2019 Sep 11;141(36):14152-14159. doi: 10.1021/jacs.9b03021. Epub 2019 Sep 3. PMID: 31150226; PMCID: PMC6774755. 3: Kang WJ, Pan HX, Wang S, Yu B, Hua H, Tang GL. Identification of the Amipurimycin Gene Cluster Yields Insight into the Biosynthesis of C9 Sugar Nucleoside Antibiotics. Org Lett. 2019 May 3;21(9):3148-3152. doi: 10.1021/acs.orglett.9b00840. Epub 2019 Apr 16. PMID: 30990701. 4: Wang S, Sun J, Zhang Q, Cao X, Zhao Y, Tang G, Yu B. Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers. Angew Chem Int Ed Engl. 2018 Mar 5;57(11):2884-2888. doi: 10.1002/anie.201800169. Epub 2018 Feb 12. PMID: 29356246. 5: Markad PR, Kumbhar N, Dhavale DD. Synthesis of the C8'-epimeric thymine pyranosyl amino acid core of amipurimycin. Beilstein J Org Chem. 2016 Aug 5;12:1765-71. doi: 10.3762/bjoc.12.165. PMID: 27559421; PMCID: PMC4979907. 6: Mane RS, Ghosh S, Chopade BA, Reiser O, Dhavale DD. Synthesis of an adenine nucleoside containing the (8'R) epimeric carbohydrate core of amipurimycin and its biological study. J Org Chem. 2011 Apr 15;76(8):2892-5. doi: 10.1021/jo102193q. Epub 2011 Mar 17. PMID: 21381774. 7: Stauffer CS, Datta A. Synthetic studies on amipurimycin: total synthesis of a thymine nucleoside analogue. J Org Chem. 2008 Jun 6;73(11):4166-74. doi: 10.1021/jo8004815. Epub 2008 May 9. PMID: 18465899. 8: Rauter A, Ferreira M, Borges C, Duarte T, Piedade F, Silva M, Santos H. Construction of a branched chain at C-3 of a hexopyranoside. Synthesis of miharamycin sugar moiety analogs. Carbohydr Res. 2000 Mar 24;325(1):1-15. doi: 10.1016/s0008-6215(99)00307-9. PMID: 10741823. 9: Rauter AP, Fernandes AC, Czernecki S, Valery JM. Deoxygenation at C-4 and Stereospecific Branched-Chain Construction at C-3 of a Methyl Hexopyranuloside. Synthetic Approach to the Amipurimycin Sugar Moiety. J Org Chem. 1996 May 31;61(11):3594-3598. doi: 10.1021/jo952220e. PMID: 11667203. 10: Goto T, Toya Y, Kondo T. Structure of amipurimycin, a new nucleoside antibiotic produced by Streptomyces novoguineensis. Nucleic Acids Symp Ser. 1980;(8):s73-4. PMID: 7255201. 11: Harada S, Kishi T. Isolation and characterization of a new nucleoside antibiotic, amipurimycin. J Antibiot (Tokyo). 1977 Jan;30(1):11-6. doi: 10.7164/antibiotics.30.11. PMID: 838627. 12: Iwasa T, Kishi T, Matsuura K, Wakae O. Streptomyces novoguineensis sp. Nov., an amipurimycin producer, and antimicrobial activity of amipurimycin. J Antibiot (Tokyo). 1977 Jan;30(1):1-10. doi: 10.7164/antibiotics.30.1. PMID: 557031.