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MedKoo Cat#: 596929 | Name: Arthrofactin

Description:

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

Arthrofactin is a lipopeptide biosurfactant.

Chemical Structure

Arthrofactin
CAS#152406-36-5

Theoretical Analysis

MedKoo Cat#: 596929

Name: Arthrofactin

CAS#: 152406-36-5

Chemical Formula: C64H111N11O20

Exact Mass: 1353.8007

Molecular Weight: 1354.64

Elemental Analysis: C, 56.75; H, 8.26; N, 11.37; O, 23.62

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
Arthrofactin;
IUPAC/Chemical Name
2,2'-((3S,6S,9S,12R,15S,18R,21R,24R,30R,33R)-6,9-di((S)-sec-butyl)-37-heptyl-27-((S)-1-hydroxyethyl)-12,18-bis(hydroxymethyl)-15,21,24,33-tetraisobutyl-2,5,8,11,14,17,20,23,26,29,32,35-dodecaoxo-1-oxa-4,7,10,13,16,19,22,25,28,31,34-undecaazacycloheptatriacontane-3,30-diyl)diacetic acid
InChi Key
HXMCERBOSXQYRH-PUWFPHIESA-N
InChi Code
InChI=1S/C64H111N11O20/c1-15-18-19-20-21-22-39-27-48(79)65-40(23-32(4)5)54(84)68-44(28-49(80)81)58(88)75-53(38(14)78)63(93)69-43(26-35(10)11)55(85)66-41(24-33(6)7)56(86)71-46(30-76)59(89)67-42(25-34(8)9)57(87)72-47(31-77)60(90)73-52(37(13)17-3)62(92)74-51(36(12)16-2)61(91)70-45(29-50(82)83)64(94)95-39/h32-47,51-53,76-78H,15-31H2,1-14H3,(H,65,79)(H,66,85)(H,67,89)(H,68,84)(H,69,93)(H,70,91)(H,71,86)(H,72,87)(H,73,90)(H,74,92)(H,75,88)(H,80,81)(H,82,83)/t36-,37-,38-,39?,40+,41+,42-,43+,44+,45-,46+,47+,51-,52-,53?/m0/s1
SMILES Code
CCCCCCCC1CC(N[C@H](CC(C)C)C(N[C@H](CC(O)=O)C(NC([C@@H](O)C)C(N[C@H](CC(C)C)C(N[C@H](CC(C)C)C(N[C@H](CO)C(N[C@@H](CC(C)C)C(N[C@H](CO)C(N[C@@H]([C@H](CC)C)C(N[C@@H]([C@H](CC)C)C(N[C@@H](CC(O)=O)C(O1)=O)=O)=O)=O)=O)=O)=O)=O)=O)=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
>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 1,354.64 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: Lange A, Sun H, Pilger J, Reinscheid UM, Gross H. Predicting the structure of cyclic lipopeptides by bioinformatics: structure revision of arthrofactin. Chembiochem. 2012 Dec 21;13(18):2671-5. doi: 10.1002/cbic.201200532. Epub 2012 Nov 21. PubMed PMID: 23169772. 2: Washio K, Lim SP, Roongsawang N, Morikawa M. A truncated form of SpoT, including the ACT domain, inhibits the production of cyclic lipopeptide arthrofactin, and is associated with moderate elevation of guanosine 3',5'-bispyrophosphate level in Pseudomonas sp. MIS38. Biosci Biotechnol Biochem. 2011;75(10):1880-8. Epub 2011 Oct 7. PubMed PMID: 21979063. 3: Washio K, Lim SP, Roongsawang N, Morikawa M. Identification and characterization of the genes responsible for the production of the cyclic lipopeptide arthrofactin by Pseudomonas sp. MIS38. Biosci Biotechnol Biochem. 2010;74(5):992-9. Epub 2010 May 7. PubMed PMID: 20460722. 4: Hirata Y, Ryu M, Oda Y, Igarashi K, Nagatsuka A, Furuta T, Sugiura M. Novel characteristics of sophorolipids, yeast glycolipid biosurfactants, as biodegradable low-foaming surfactants. J Biosci Bioeng. 2009 Aug;108(2):142-6. doi: 10.1016/j.jbiosc.2009.03.012. PubMed PMID: 19619862. 5: Lim SP, Roongsawang N, Washio K, Morikawa M. Flexible exportation mechanisms of arthrofactin in Pseudomonas sp. MIS38. J Appl Microbiol. 2009 Jul;107(1):157-66. doi: 10.1111/j.1365-2672.2009.04189.x. Epub 2009 Mar 3. PubMed PMID: 19302333. 6: Das P, Mukherjee S, Sen R. Genetic regulations of the biosynthesis of microbial surfactants: an overview. Biotechnol Genet Eng Rev. 2008;25:165-85. Review. PubMed PMID: 21412355. 7: Lim SP, Roongsawang N, Washio K, Morikawa M. Functional analysis of a pyoverdine synthetase from Pseudomonas sp. MIS38. Biosci Biotechnol Biochem. 2007 Aug;71(8):2002-9. Epub 2007 Aug 7. PubMed PMID: 17690457. 8: Roongsawang N, Washio K, Morikawa M. In vivo characterization of tandem C-terminal thioesterase domains in arthrofactin synthetase. Chembiochem. 2007 Mar 26;8(5):501-12. PubMed PMID: 17328008. 9: Balibar CJ, Vaillancourt FH, Walsh CT. Generation of D amino acid residues in assembly of arthrofactin by dual condensation/epimerization domains. Chem Biol. 2005 Nov;12(11):1189-200. PubMed PMID: 16298298. 10: Roongsawang N, Hase Ki, Haruki M, Imanaka T, Morikawa M, Kanaya S. Cloning and characterization of the gene cluster encoding arthrofactin synthetase from Pseudomonas sp. MIS38. Chem Biol. 2003 Sep;10(9):869-80. PubMed PMID: 14522057. 11: Morikawa M, Hirata Y, Imanaka T. A study on the structure-function relationship of lipopeptide biosurfactants. Biochim Biophys Acta. 2000 Nov 15;1488(3):211-8. PubMed PMID: 11082531. 12: Morikawa M, Daido H, Pongpobpibool S, Imanaka T. Construction of a new host-vector system in Arthrobacter sp. and cloning of the lipase gene. Appl Microbiol Biotechnol. 1994 Nov;42(2-3):300-3. PubMed PMID: 7765770. 13: Morikawa M, Daido H, Takao T, Murata S, Shimonishi Y, Imanaka T. A new lipopeptide biosurfactant produced by Arthrobacter sp. strain MIS38. J Bacteriol. 1993 Oct;175(20):6459-66. PubMed PMID: 8407822; PubMed Central PMCID: PMC206754.