Amipurimycin

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

MedKoo CAT#: 463013

CAS#: 61991-08-0

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

Chemical Structure

img
Amipurimycin
CAS# 61991-08-0
Instruction

Theoretical Analysis

MedKoo Cat#: 463013
Name: Amipurimycin
CAS#: 61991-08-0
Chemical Formula: C20H29N7O8
Exact Mass: 495.21
Molecular Weight: 495.493
Elemental Analysis: C, 48.48; H, 5.90; N, 19.79; O, 25.83

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.