A 26771B

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

MedKoo CAT#: 571249

CAS#: 56448-20-5

Description: A 26771B is a macrolide lactone antibiotic.


Price and Availability

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A 26771B 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#: 571249
Name: A 26771B
CAS#: 56448-20-5
Chemical Formula: C20H30O7
Exact Mass: 382.1992
Molecular Weight: 382.45
Elemental Analysis: C, 62.81; H, 7.91; O, 29.28


Synonym: A 26771B; A-26771B; A26771B

IUPAC/Chemical Name: 4-(((6S,16R,E)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl)oxy)-4-oxobutanoic acid

InChi Key: CAOCHWFVLJETKN-SADTYBKJSA-N

InChi Code: InChI=1S/C20H30O7/c1-15-9-7-5-3-2-4-6-8-10-17(16(21)11-13-19(24)26-15)27-20(25)14-12-18(22)23/h11,13,15,17H,2-10,12,14H2,1H3,(H,22,23)/b13-11+/t15-,17+/m1/s1

SMILES Code: O=C(O[C@@H]1C(/C=C/C(O[C@H](C)CCCCCCCCC1)=O)=O)CCC(O)=O


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: Canova S, Lépine R, Thys A, Baron A, Roche D. Synthesis and biological properties of macrolactam analogs of the natural product macrolide (-)-A26771B. Bioorg Med Chem Lett. 2011 Aug 15;21(16):4768-72. doi: 10.1016/j.bmcl.2011.06.073. Epub 2011 Jun 23. PubMed PMID: 21767951.

2: Michel KH, Demarco PV, Nagarjan R. The isolation and structure elucidation of macrocyclic lactone antibiotic, A26771B. J Antibiot (Tokyo). 1977 Jul;30(7):571-5. PubMed PMID: 142754.

3: Persich P, Llaveria J, Lhermet R, de Haro T, Stade R, Kondoh A, Fürstner A. Increasing the structural span of alkyne metathesis. Chemistry. 2013 Sep 23;19(39):13047-58. doi: 10.1002/chem.201302320. Epub 2013 Sep 3. PubMed PMID: 24038738.

4: Gebauer J, Blechert S. Synthesis of gamma,delta-unsaturated-beta-keto lactones via sequential cross metathesis-lactonization: a facile entry to macrolide antibiotic (-)-A26771B. J Org Chem. 2006 Mar 3;71(5):2021-5. PubMed PMID: 16496989.

5: Stierle AA, Stierle DB, Decato D, Priestley ND, Alverson JB, Hoody J, McGrath K, Klepacki D. The Berkeleylactones, Antibiotic Macrolides from Fungal Coculture. J Nat Prod. 2017 Apr 28;80(4):1150-1160. doi: 10.1021/acs.jnatprod.7b00133. Epub 2017 Mar 22. PubMed PMID: 28326781; PubMed Central PMCID: PMC5467647.

6: Kobayashi Y, Okui H. An efficient synthesis of antibiotic (-)-A26771B. J Org Chem. 2000 Jan 28;65(2):612-5. PubMed PMID: 10813983.