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840521P

Avanti

18:1 Lysyl PG

Avanti Research™ - A Croda Brand

Synonym(s):

Lysyl-DOPG

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About This Item

Empirical Formula (Hill Notation):
C48H93Cl2N2O11P
CAS Number:
1246303-07-0
Molecular Weight:
976.14
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

18:1 Lysyl PG, 1,2-dioleoyl-sn-glycero-3-[phospho-rac-(3-lysyl(1-glycerol))] (chloride salt), powder

InChI

1S/C48H91N2O11P.2ClH/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-36-46(52)57-41-44(42-60-62(55,56)59-40-43(51)39-58-48(54)45(50)35-33-34-38-49)61-47(53)37-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;;/h17-20,43-45,51H,3-16,21-42,49-50H2,1-2H3,(H,55,56);2*

InChI key

QLNZUMYQGKEYKU-CIZZXKMDSA-N

SMILES string

OC(COC([C@@](CCCC[NH3+])([H])[NH3+])=O)COP(O)(OC[C@]([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)=O.[Cl-].[Cl-]

assay

>99% (up to 15% acyl migration on lysine, TLC)

form

powder

packaging

pkg of 1 × 1 mg (840521P-1mg)
pkg of 1 × 10 mg (840521P-10mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 840521P

lipid type

phospholipids
bioactive lipids

shipped in

dry ice

storage temp.

−20°C

Packaging

5 mL Clear Glass Sealed Ampule (840521P-10mg)
5 mL Amber Glass Screw Cap Vial (840521P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Application

18:1 Lysyl PG is suitable to prepare liposome solutions.

Biochem/physiol Actions

Lysyl-phosphatidylglycerol (lysyl-PG) in the cytoplasmic membranes of Staphylococcus is associated with improved resistance to antibiotics, like daptomycin and host defense antimicrobial peptides.

General description

18:1 Lysyl PG/1,2-dioleoyl-sn-glycero-3-[phospho-rac-(3-lysyl(1-glycerol))] (lysyl-DOPG) is a synthetic phospholipid. It has a lysine group, added to the terminal glycerol of DOPG. Lysyl-phosphatidylglycerol (LPG), a membrane lipid is mainly seen in gram-positive bacteria. It is cationic phospholipid.

Storage Class

11 - Combustible Solids

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Lysyl-phosphatidylglycerol attenuates membrane perturbation rather than surface association of the cationic antimicrobial peptide 6W-RP-1 in a model membrane system: implications for daptomycin resistance
Kilelee E, et al.
Antimicrobial Agents and Chemotherapy, 54(10), 4476-4479 (2010)
The lipid lysyl-phosphatidylglycerol is present in membranes of Rhizobium tropici CIAT899 and confers increased resistance to polymyxin B under acidic growth conditions
Sohlenkamp C, et al.
Molecular plant-microbe interactions : MPMI, 20(11), 1421-1430 (2007)
Helix stabilization precedes aqueous and bilayer-catalyzed fiber formation in islet amyloid polypeptide
Williamson JA, et al.
Journal of molecular biology, 393(2), 383-396 (2009)
Christian Sohlenkamp et al.
Molecular plant-microbe interactions : MPMI, 20(11), 1421-1430 (2007-11-06)
Lysyl-phosphatidylglycerol (LPG) is a well-known membrane lipid in several gram-positive bacteria but is almost unheard of in gram-negative bacteria. In Staphylococcus aureus, the gene product of mprF is responsible for LPG formation. Low pH-inducible genes, termed IpiA, have been identified
Lipid bilayer modules as determinants of K+ channel gating
Syeda R, et al.
Test, 289(7), 4233-4243 (2014)

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