MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 598963 | Name: Lipopeptin A

Description:

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

Lipopeptin A is a lipoprotein subclass. Genetic studies and numerous epidemiologic studies have identified Lp(a) as a risk factor for atherosclerotic diseases such as coronary heart disease and stroke.

Chemical Structure

Lipopeptin A
CAS#73666-47-4

Theoretical Analysis

MedKoo Cat#: 598963

Name: Lipopeptin A

CAS#: 73666-47-4

Chemical Formula: C54H84N10O19

Exact Mass: 1176.5914

Molecular Weight: 1177.31

Elemental Analysis: C, 55.09; H, 7.19; N, 11.90; O, 25.82

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Lipopeptin A; Lipopeptin A, dihydrate;
IUPAC/Chemical Name
3-(6-(3-amino-1-hydroxy-3-oxopropyl)-12-(2-amino-2-oxoethyl)-9-benzyl-21-(carboxymethyl)-15,18-bis(hydroxymethyl)-10,13,25-trimethyl-24-(12-methyltetradecanamido)-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosan-3-yl)propanoic acid
InChi Key
AXMACOGXBDPVJT-UHFFFAOYSA-N
InChi Code
InChI=1S/C54H84N10O19/c1-6-30(2)18-14-11-9-7-8-10-12-17-21-42(70)61-45-31(3)83-54(82)33(22-23-43(71)72)57-51(79)46(39(67)27-41(56)69)62-49(77)37(24-32-19-15-13-16-20-32)63(4)53(81)38(26-40(55)68)64(5)52(80)36(29-66)60-48(76)35(28-65)59-47(75)34(25-44(73)74)58-50(45)78/h13,15-16,19-20,30-31,33-39,45-46,65-67H,6-12,14,17-18,21-29H2,1-5H3,(H2,55,68)(H2,56,69)(H,57,79)(H,58,78)(H,59,75)(H,60,76)(H,61,70)(H,62,77)(H,71,72)(H,73,74)
SMILES Code
CCC(CCCCCCCCCCC(NC1C(C)OC(C(CCC(O)=O)NC(C(C(O)CC(N)=O)NC(C(Cc2ccccc2)N(C)C(C(CC(N)=O)N(C)C(C(CO)NC(C(CO)NC(C(CC(O)=O)NC1=O)=O)=O)=O)=O)=O)=O)=O)=O)C
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,177.31 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: Castelletto V, Hamley IW, Reza M, Ruokolainen J. Interactions between lipid-free apolipoprotein-AI and a lipopeptide incorporating the RGDS cell adhesion motif. Nanoscale. 2015 Jan 7;7(1):171-8. doi: 10.1039/c4nr05072j. PubMed PMID: 25406726. 2: Perez-Ameneiro M, Vecino X, Cruz JM, Moldes AB. Wastewater treatment enhancement by applying a lipopeptide biosurfactant to a lignocellulosic biocomposite. Carbohydr Polym. 2015 Oct 20;131:186-96. doi: 10.1016/j.carbpol.2015.05.075. Epub 2015 Jun 9. PubMed PMID: 26256175. 3: Sharma D, Mandal SM, Manhas RK. Purification and characterization of a novel lipopeptide from Streptomyces amritsarensis sp. nov. active against methicillin-resistant Staphylococcus aureus. AMB Express. 2014 Jun 28;4:50. doi: 10.1186/s13568-014-0050-y. eCollection 2014. PubMed PMID: 25006539; PubMed Central PMCID: PMC4077001. 4: Stiehm M, Peters K, Wiesmüller KH, Bufe A, Peters M. A novel synthetic lipopeptide is allergy-protective by the induction of LPS-tolerance. Clin Exp Allergy. 2013 Jul;43(7):785-97. doi: 10.1111/cea.12116. PubMed PMID: 23786285. 5: Mnif I, Hammami I, Triki MA, Azabou MC, Ellouze-Chaabouni S, Ghribi D. Antifungal efficiency of a lipopeptide biosurfactant derived from Bacillus subtilis SPB1 versus the phytopathogenic fungus, Fusarium solani. Environ Sci Pollut Res Int. 2015 Nov;22(22):18137-47. doi: 10.1007/s11356-015-5005-6. Epub 2015 Jul 16. PubMed PMID: 26178831. 6: Poitevin M, Tranquart F, Cherkaoui S. Use of capillary electrophoresis as a versatile tool to measure interaction constants between a KDR-binding PEGylated lipopeptide and pegylated phospholipid micelles. Electrophoresis. 2015 Jan;36(2):326-34. doi: 10.1002/elps.201400280. Epub 2014 Nov 4. PubMed PMID: 25257539. 7: Kalai-Grami L, Karkouch I, Naili O, Slimene IB, Elkahoui S, Zekri RB, Touati I, Mnari-Hattab M, Hajlaoui MR, Limam F. Production and identification of iturin A lipopeptide from Bacillus methyltrophicus TEB1 for control of Phoma tracheiphila. J Basic Microbiol. 2016 Aug;56(8):864-71. doi: 10.1002/jobm.201500683. Epub 2016 Apr 29. PubMed PMID: 27125201. 8: Akazawa T, Ohashi T, Nakajima H, Nishizawa Y, Kodama K, Sugiura K, Inaba T, Inoue N. Development of a dendritic cell-targeting lipopeptide as an immunoadjuvant that inhibits tumor growth without inducing local inflammation. Int J Cancer. 2014 Dec 15;135(12):2847-56. doi: 10.1002/ijc.28939. Epub 2014 May 14. PubMed PMID: 24789268. 9: Wang S, Shen Y, Zhang J, Xu S, Liu H. A designed lipopeptide with a leucine zipper as an imbedded on/off switch for lipid bilayers. Phys Chem Chem Phys. 2016 Apr 21;18(15):10129-37. doi: 10.1039/c6cp00378h. Epub 2016 Mar 24. PubMed PMID: 27009364. 10: Masaka T, Li Y, Kawatobi S, Koide Y, Takami A, Yano K, Imai R, Yagi N, Suzuki H, Hikawa H, Tatsuno I, Terada K, Yokoyama Y. [Liposome modified with VIP-lipopeptide as a new drug delivery system]. Yakugaku Zasshi. 2014;134(9):987-95. Japanese. PubMed PMID: 25174370. 11: Hajfarajollah H, Mokhtarani B, Noghabi KA. Newly antibacterial and antiadhesive lipopeptide biosurfactant secreted by a probiotic strain, Propionibacterium freudenreichii. Appl Biochem Biotechnol. 2014 Dec;174(8):2725-40. doi: 10.1007/s12010-014-1221-7. Epub 2014 Sep 13. PubMed PMID: 25216696. 12: Hajare SN, Subramanian M, Gautam S, Sharma A. Induction of apoptosis in human cancer cells by a Bacillus lipopeptide bacillomycin D. Biochimie. 2013 Sep;95(9):1722-31. doi: 10.1016/j.biochi.2013.05.015. Epub 2013 Jun 14. PubMed PMID: 23770444. 13: McKeown SC, Zecri FJ, Fortier E, Taggart A, Sviridenko L, Adams CM, McAllister KH, Pin SS. The design and implementation of a generic lipopeptide scanning platform to enable the identification of 'locally acting' agonists for the apelin receptor. Bioorg Med Chem Lett. 2014 Oct 15;24(20):4871-5. doi: 10.1016/j.bmcl.2014.08.045. Epub 2014 Aug 28. PubMed PMID: 25241924. 14: Rao M, Wei W, Ge M, Chen D, Sheng X. A new antibacterial lipopeptide found by UPLC-MS from an actinomycete Streptomyces sp. HCCB10043. Nat Prod Res. 2013;27(23):2190-5. doi: 10.1080/14786419.2013.811661. Epub 2013 Jul 1. PubMed PMID: 23815473. 15: Sharafi H, Abdoli M, Hajfarajollah H, Samie N, Alidoust L, Abbasi H, Fooladi J, Zahiri HS, Noghabi KA. First report of a lipopeptide biosurfactant from thermophilic bacterium Aneurinibacillus thermoaerophilus MK01 newly isolated from municipal landfill site. Appl Biochem Biotechnol. 2014 Jul;173(5):1236-49. doi: 10.1007/s12010-014-0928-9. Epub 2014 May 1. PubMed PMID: 24781982. 16: Velkov T, Yun B, Schneider EK, Azad MA, Dolezal O, Morris FC, Nation RL, Wang J, Chen K, Yu HH, Wang L, Thompson PE, Roberts KD, Li J. A Novel Chemical Biology Approach for Mapping of Polymyxin Lipopeptide Antibody Binding Epitopes. ACS Infect Dis. 2016 May 13;2(5):341-51. doi: 10.1021/acsinfecdis.6b00031. Epub 2016 Mar 29. PubMed PMID: 27627202; PubMed Central PMCID: PMC5321607. 17: 't Hart P, Kleijn LH, de Bruin G, Oppedijk SF, Kemmink J, Martin NI. A combined solid- and solution-phase approach provides convenient access to analogues of the calcium-dependent lipopeptide antibiotics. Org Biomol Chem. 2014 Feb 14;12(6):913-8. doi: 10.1039/c3ob42238k. PubMed PMID: 24346297. 18: Baltz RH. Combinatorial biosynthesis of cyclic lipopeptide antibiotics: a model for synthetic biology to accelerate the evolution of secondary metabolite biosynthetic pathways. ACS Synth Biol. 2014 Oct 17;3(10):748-58. doi: 10.1021/sb3000673. Epub 2012 Aug 23. Review. PubMed PMID: 23654258. 19: Ajesh K, Sudarslal S, Arunan C, Sreejith K. Kannurin, a novel lipopeptide from Bacillus cereus strain AK1: isolation, structural evaluation and antifungal activities. J Appl Microbiol. 2013 Dec;115(6):1287-96. doi: 10.1111/jam.12324. Epub 2013 Sep 2. PubMed PMID: 23937170. 20: Liu R, Wang J, Yang Y, Khan I, Zhu N. Rabies virus lipopeptide conjugated to a TLR7 agonist improves the magnitude and quality of the Th1-biased humoral immune response in mice. Virology. 2016 Oct;497:102-110. doi: 10.1016/j.virol.2016.06.019. Epub 2016 Jul 21. PubMed PMID: 27449478.

View History

Tolboxane

Tolboxane