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MedKoo Cat#: 571224 | Name: Streptomyces A-Factor

Description:

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

Streptomyces A-Factor is a microbial hormone found in Streptomyces griseus, A-factor at an extremely low concentration triggers streptomycin biosynthesis and cell differentiation by binding a repressor-type receptor protein (ArpA) and dissociating it from DNA. A factor plays a role in allowing the cell to grow healthy and to produce antibiotics in response to environmental conditions.

Chemical Structure

Streptomyces A-Factor
Streptomyces A-Factor
CAS#51311-41-2

Theoretical Analysis

MedKoo Cat#: 571224

Name: Streptomyces A-Factor

CAS#: 51311-41-2

Chemical Formula: C13H22O4

Exact Mass: 242.1518

Molecular Weight: 242.32

Elemental Analysis: C, 64.44; H, 9.15; O, 26.41

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 #
No Data
Synonym
Streptomyces A-Factor; A-Factor (Lactone)
IUPAC/Chemical Name
(3S,4R)-4-(hydroxymethyl)-3-(6-methylheptanoyl)dihydrofuran-2(3H)-one
InChi Key
REAWNMHCBIUKLZ-PWSUYJOCSA-N
InChi Code
InChI=1S/C13H22O4/c1-9(2)5-3-4-6-11(15)12-10(7-14)8-17-13(12)16/h9-10,12,14H,3-8H2,1-2H3/t10-,12+/m1/s1
SMILES Code
O=C1OC[C@@H](CO)[C@H]1C(CCCCC(C)C)=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 242.32 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: Matselyukh B, Mohammadipanah F, Laatsch H, Rohr J, Efremenkova O, Khilya V. N-methylphenylalanyl-dehydrobutyrine diketopiperazine, an A-factor mimic that restores antibiotic biosynthesis and morphogenesis in Streptomyces globisporus 1912-B2 and Streptomyces griseus 1439. J Antibiot (Tokyo). 2015 Jan;68(1):9-14. doi: 10.1038/ja.2014.86. Epub 2014 Jul 9. PubMed PMID: 25005816. 2: Hara O, Beppu T. Induction of streptomycin-inactivating enzyme by A-factor in Streptomyces griseus. J Antibiot (Tokyo). 1982 Sep;35(9):1208-15. PubMed PMID: 6292150. 3: Yao MD, Ohtsuka J, Nagata K, Miyazono K, Zhi Y, Ohnishi Y, Tanokura M. Complex structure of the DNA-binding domain of AdpA, the global transcription factor in Streptomyces griseus, and a target duplex DNA reveals the structural basis of its tolerant DNA sequence specificity. J Biol Chem. 2013 Oct 25;288(43):31019-29. doi: 10.1074/jbc.M113.473611. Epub 2013 Sep 9. PubMed PMID: 24019524; PubMed Central PMCID: PMC3829415. 4: Chi WJ, Jin XM, Jung SC, Oh EA, Hong SK. Characterization of Sgr3394 produced only by the A-factor-producin Streptomyces griseus IFO 13350, not by the A-factor deficient mutant. J Microbiol. 2011 Feb;49(1):155-60. doi: 10.1007/s12275-011-0330-z. Epub 2011 Mar 3. PubMed PMID: 21369994. 5: Tan GY, Bai L, Zhong JJ. Exogenous 1,4-butyrolactone stimulates A-factor-like cascade and validamycin biosynthesis in Streptomyces hygroscopicus 5008. Biotechnol Bioeng. 2013 Nov;110(11):2984-93. doi: 10.1002/bit.24965. Epub 2013 Aug 2. PubMed PMID: 23703669. 6: Hara O, Horinouchi S, Uozumi T, Beppu T. Genetic analysis of A-factor synthesis in Streptomyces coelicolor A3(2) and Streptomyces griseus. J Gen Microbiol. 1983 Sep;129(9):2939-44. PubMed PMID: 6415235. 7: Horinouchi S. A microbial hormone, A-factor, as a master switch for morphological differentiation and secondary metabolism in Streptomyces griseus. Front Biosci. 2002 Oct 1;7:d2045-57. Review. PubMed PMID: 12165483. 8: Miyake K, Horinouchi S, Yoshida M, Chiba N, Mori K, Nogawa N, Morikawa N, Beppu T. Detection and properties of A-factor-binding protein from Streptomyces griseus. J Bacteriol. 1989 Aug;171(8):4298-302. PubMed PMID: 2502536; PubMed Central PMCID: PMC210204. 9: Ando N, Matsumori N, Sakuda S, Beppu T, Horinouchi S. Involvement of afsA in A-factor biosynthesis as a key enzyme. J Antibiot (Tokyo). 1997 Oct;50(10):847-52. PubMed PMID: 9402990. 10: Morin JB, Adams KL, Sello JK. Replication of biosynthetic reactions enables efficient synthesis of A-factor, a γ-butyrolactone autoinducer from Streptomyces griseus. Org Biomol Chem. 2012 Feb 28;10(8):1517-20. doi: 10.1039/c2ob06653j. Epub 2012 Jan 16. PubMed PMID: 22246070. 11: Yao MD, Miyazono K, Ohtsuka J, Hirano S, Nagata K, Horinouchi S, Ohnishi Y, Tanokura M. Purification, crystallization and preliminary X-ray analysis of the DNA-binding domain of AdpA, the central transcription factor in the A-factor regulatory cascade in the filamentous bacterium Streptomyces griseus, in complex with a duplex DNA. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2012 Aug 1;68(Pt 8):946-9. doi: 10.1107/S1744309112026899. Epub 2012 Jul 31. PubMed PMID: 22869129; PubMed Central PMCID: PMC3412780. 12: Onaka H, Sugiyama M, Horinouchi S. A mutation at proline-115 in the A-factor receptor protein of Streptomyces griseus abolishes DNA-binding ability but not ligand-binding ability. J Bacteriol. 1997 Apr;179(8):2748-52. PubMed PMID: 9098075; PubMed Central PMCID: PMC179026. 13: Horinouchi S, Ohnishi Y, Kang DK. The A-factor regulatory cascade and cAMP in the regulation of physiological and morphological development in Streptomyces griseus. J Ind Microbiol Biotechnol. 2001 Sep;27(3):177-82. Review. PubMed PMID: 11780789. 14: Ueda K, Umeyama T, Beppu T, Horinouchi S. The aerial mycelium-defective phenotype of Streptomyces griseus resulting from A-factor deficiency is suppressed by a Ser/Thr kinase of S. coelicolor A3(2). Gene. 1996 Feb 22;169(1):91-5. PubMed PMID: 8635757. 15: Gruzina VD, Gorbatiuk EV, Efremenkova OV, Filippova SN, El'-Registan GI, Dudnik IuV. [A new regulatory function of the A-factor--stimulation of the streptomyces spore germination]. Mikrobiologiia. 2003 Nov-Dec;72(6):770-4. Russian. PubMed PMID: 14768543. 16: Beppu T, Horinouchi S. Molecular mechanisms of the A-factor-dependent control of secondary metabolism in Streptomyces. Planta Med. 1991 Oct;57(7):S44-7. Review. PubMed PMID: 1956957. 17: Vasilenko TI, Tovarova II, Khokhlov AS. [Effect of the A-factor on the adenylate level in Streptomyces griseus]. Prikl Biokhim Mikrobiol. 1983 May-Jun;19(3):356-61. Russian. PubMed PMID: 6410372. 18: Birkó Z, Swiatek M, Szájli E, Medzihradszky KF, Vijgenboom E, Penyige A, Keseru J, van Wezel GP, Biró S. Lack of A-factor production induces the expression of nutrient scavenging and stress-related proteins in Streptomyces griseus. Mol Cell Proteomics. 2009 Oct;8(10):2396-403. doi: 10.1074/mcp.M900194-MCP200. Epub 2009 Jul 22. PubMed PMID: 19625340; PubMed Central PMCID: PMC2758764. 19: Recio E, Colinas A, Rumbero A, Aparicio JF, Martín JF. PI factor, a novel type quorum-sensing inducer elicits pimaricin production in Streptomyces natalensis. J Biol Chem. 2004 Oct 1;279(40):41586-93. Epub 2004 Jul 1. PubMed PMID: 15231842. 20: Birkó Z, Bialek S, Buzás K, Szájli E, Traag BA, Medzihradszky KF, Rigali S, Vijgenboom E, Penyige A, Kele Z, van Wezel GP, Biró S. The secreted signaling protein factor C triggers the A-factor response regulon in Streptomyces griseus: overlapping signaling routes. Mol Cell Proteomics. 2007 Jul;6(7):1248-56. Epub 2007 Mar 20. PubMed PMID: 17376769.

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