Lysylphosphatidylglycerol | CAS#42241-11-2 | membrane phospholipid

MedKoo Cat#: 597523 | Name: Lysylphosphatidylglycerol

Description:

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

Lysylphosphatidylglycerol is glycerol with two fatty acids plus a lysine-glycerol-phosphate; a major membrane phospholipid of Staphylococcus; the lysine positive charge repels DEFENSINS.

Chemical Structure

Lysylphosphatidylglycerol

CAS#42241-11-2

Theoretical Analysis

MedKoo Cat#: 597523

Name: Lysylphosphatidylglycerol

CAS#: 42241-11-2

Chemical Formula: C9H21N2O7P

Exact Mass: 300.1086

Molecular Weight: 300.24

Elemental Analysis: C, 36.00; H, 7.05; N, 9.33; O, 37.30; P, 10.32

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

Lysylphosphatidylglycerol;

IUPAC/Chemical Name

(S)-2,6-diaminohexanoic (2,3-dihydroxypropyl phosphoric) anhydride

InChi Key

FGYYWCMRFGLJOB-MQWKRIRWSA-N

InChi Code

InChI=1S/C9H21N2O7P/c10-4-2-1-3-8(11)9(14)18-19(15,16)17-6-7(13)5-12/h7-8,12-13H,1-6,10-11H2,(H,15,16)/t7?,8-/m0/s1

SMILES Code

NCCCC[C@H](N)C(OP(O)(OCC(O)CO)=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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 300.24 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.

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: Atila M, Katselis G, Chumala P, Luo Y. Characterization of N-Succinylation of L-Lysylphosphatidylglycerol in Bacillus subtilis Using Tandem Mass Spectrometry. J Am Soc Mass Spectrom. 2016 Oct;27(10):1606-13. doi: 10.1007/s13361-016-1455-4. Epub 2016 Aug 9. PubMed PMID: 27506207. 2: Staubitz P, Neumann H, Schneider T, Wiedemann I, Peschel A. MprF-mediated biosynthesis of lysylphosphatidylglycerol, an important determinant in staphylococcal defensin resistance. FEMS Microbiol Lett. 2004 Feb 9;231(1):67-71. PubMed PMID: 14769468. 3: Bandyopadhyay A, McCarthy KA, Kelly MA, Gao J. Targeting bacteria via iminoboronate chemistry of amine-presenting lipids. Nat Commun. 2015 Mar 12;6:6561. doi: 10.1038/ncomms7561. PubMed PMID: 25761996; PubMed Central PMCID: PMC4363082. 4: Gould RM, Dawson RM. The trypsin-catalyzed hydrolysis of monomolecular films of lysylphosphatidylglycerol. Biochim Biophys Acta. 1972 Oct 23;288(1):1-11. PubMed PMID: 4640386. 5: Short SA, White DC. Metabolism of phosphatidylglycerol, lysylphosphatidylglycerol, and cardiolipin of Staphylococcus aureus. J Bacteriol. 1971 Oct;108(1):219-26. PubMed PMID: 5122804; PubMed Central PMCID: PMC247054. 6: Tocanne JF, Verheij HM, den Kamp JA, van Deenen LL. Chemical and physicochemical studies of lysylphosphatidylglycerol derivatives. Occurrence of a2' yields 3' lysyl migration. Chem Phys Lipids. 1974 Dec;13(4):389-403. PubMed PMID: 4452218. 7: Khatib TO, Stevenson H, Yeaman MR, Bayer AS, Pokorny A. Binding of Daptomycin to Anionic Lipid Vesicles Is Reduced in the Presence of Lysyl-Phosphatidylglycerol. Antimicrob Agents Chemother. 2016 Jul 22;60(8):5051-3. doi: 10.1128/AAC.00744-16. Print 2016 Aug. PubMed PMID: 27216066; PubMed Central PMCID: PMC4958220. 8: Hebecker S, Krausze J, Hasenkampf T, Schneider J, Groenewold M, Reichelt J, Jahn D, Heinz DW, Moser J. Structures of two bacterial resistance factors mediating tRNA-dependent aminoacylation of phosphatidylglycerol with lysine or alanine. Proc Natl Acad Sci U S A. 2015 Aug 25;112(34):10691-6. doi: 10.1073/pnas.1511167112. Epub 2015 Aug 10. PubMed PMID: 26261323; PubMed Central PMCID: PMC4553816. 9: Lennarz WJ, Bonsen PP, van Deenen LL. Substrate specificity of O-L-lysylphosphatidylglycerol synthetase. Enzymatic studies on the structure of O-L-lysylphosphatidylglycerol. Biochemistry. 1967 Aug;6(8):2307-12. PubMed PMID: 6049461. 10: Rosado H, Turner RD, Foster SJ, Taylor PW. Impact of the β-Lactam Resistance Modifier (-)-Epicatechin Gallate on the Non-Random Distribution of Phospholipids across the Cytoplasmic Membrane of Staphylococcus aureus. Int J Mol Sci. 2015 Jul 23;16(8):16710-27. doi: 10.3390/ijms160816710. PubMed PMID: 26213914; PubMed Central PMCID: PMC4581164. 11: Dare K, Shepherd J, Roy H, Seveau S, Ibba M. LysPGS formation in Listeria monocytogenes has broad roles in maintaining membrane integrity beyond antimicrobial peptide resistance. Virulence. 2014 May 15;5(4):534-46. doi: 10.4161/viru.28359. Epub 2014 Mar 6. PubMed PMID: 24603093; PubMed Central PMCID: PMC4063814. 12: Lee KC, Kim KK, Kim JS, Kim DS, Ko SH, Yang SH, Lee JS. Cohnella collisoli sp. nov., isolated from lava forest soil. Int J Syst Evol Microbiol. 2015 Sep;65(9):3125-30. doi: 10.1099/ijsem.0.000388. Epub 2015 Jun 25. PubMed PMID: 26296691. 13: Goldfine H. Charge counter charge: bacterial response to antimicrobial cationic peptides and more. Virulence. 2014 May 15;5(4):451-3. doi: 10.4161/viru.28662. Epub 2014 Apr 4. PubMed PMID: 24705072; PubMed Central PMCID: PMC4063804. 14: Tocanne JF, Ververgaert PH, Verkleij AJ, van Deenen LL. A monolayer and freeze-etching study of charged phospholipids. II. Ionic properties of mixtures of phosphatidylglycerol and lysylphosphatidylglycerol. Chem Phys Lipids. 1974 May;12(3):220-31. PubMed PMID: 4838050. 15: Tocanne JF, Ververgaert PH, Verkleij AJ, van Deenen LL. A monolayer and freeze-etching study of charged phospholipids. I. Effects of ions and pH on the ionic properties of phosphatidylglycerol and lysylphosphatidylglycerol. Chem Phys Lipids. 1974 May;12(3):201-19. PubMed PMID: 4135141. 16: Dennison SR, Morton LH, Harris F, Phoenix DA. Low pH Enhances the Action of Maximin H5 against Staphylococcus aureus and Helps Mediate Lysylated Phosphatidylglycerol-Induced Resistance. Biochemistry. 2016 Jul 12;55(27):3735-51. doi: 10.1021/acs.biochem.6b00101. Epub 2016 Jul 1. PubMed PMID: 27336672. 17: Johnson CM, Grossman AD. The Composition of the Cell Envelope Affects Conjugation in Bacillus subtilis. J Bacteriol. 2016 Mar 31;198(8):1241-9. doi: 10.1128/JB.01044-15. Print 2016 Apr. PubMed PMID: 26833415; PubMed Central PMCID: PMC4859586. 18: Kuhn S, Slavetinsky CJ, Peschel A. Synthesis and function of phospholipids in Staphylococcus aureus. Int J Med Microbiol. 2015 Feb;305(2):196-202. doi: 10.1016/j.ijmm.2014.12.016. Epub 2014 Dec 23. Review. PubMed PMID: 25595024. 19: Chen YF, Sun TL, Sun Y, Huang HW. Interaction of daptomycin with lipid bilayers: a lipid extracting effect. Biochemistry. 2014 Aug 26;53(33):5384-92. doi: 10.1021/bi500779g. Epub 2014 Aug 11. PubMed PMID: 25093761; PubMed Central PMCID: PMC4148140. 20: Atila M, Luo Y. Profiling and tandem mass spectrometry analysis of aminoacylated phospholipids in Bacillus subtilis . Version 2. F1000Res. 2016 Jan 29 [revised 2016 Jan 1];5:121. doi: 10.12688/f1000research.7842.2. eCollection 2016. PubMed PMID: 26998233; PubMed Central PMCID: PMC4792211.