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840520P

Avanti

16:0 Lysyl PG

Avanti Research™ - A Croda Brand

Synonym(s):

Lysyl-DPPG

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About This Item

Empirical Formula (Hill Notation):
C44H89Cl2N2O11P
CAS Number:
1246303-06-9
Molecular Weight:
924.06
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

16:0 Lysyl PG, Avanti Research™ - A Croda Brand

InChI

1S/C44H87N2O11P.2ClH/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-32-42(48)53-37-40(57-43(49)33-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-56-58(51,52)55-36-39(47)35-54-44(50)41(46)31-29-30-34-45;;/h39-41,47H,3-38,45-46H2,1-2H3,(H,51,52);2*1H/t39?,40-,41+;;/m1../s

InChI key

CDKVLSICTGSTLD-WEQCYVBHSA-N

SMILES string

OC(COC([C@@](CCCC[NH3+])([H])[NH3+])=O)COP(O)(OC[C@]([H])(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O)=O.[Cl-].[Cl-]

description

1,2-dipalmitoyl-sn-glycero-3-[phospho-rac-(3-lysyl(1-glycerol))] (chloride salt)

assay

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

form

powder

packaging

pkg of 1 × 1 mg (840520P-1mg)
pkg of 1 × 5 mg (840520P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

lipid type

bioactive lipids
phospholipids

shipped in

dry ice

storage temp.

−20°C

Application

16:0 Lysyl PG is suitable for use:
  • as a standard for lipidomics analysis by using three-dimensional hydrophilic interaction liquid chromatography-ion mobility-mass spectrometry (HILIC-IM-MS)
  • to analyse the influence of peptides on the phase transition behavior of lipids by fourier transform infrared spectroscopy
  • in the preparation of artificial vesicles modelled on the lipid composition of Staphylococcal membranes to study the effect of galloyl catechins

Biochem/physiol Actions

Lysyl phosphatidylglycerol (Lysyl-PG) is formed by lysinylation of PG in the presence of multiprotein resistance factor (MprF). MprF flips lysyl-PG from inner to outer membrane leaflet, increasing the positive charge on the membrane. Lysyl PG is essential for domain formation and antibiotic resistance.

General description

Lysyl PG is one of the predominant lipid constituents of gram-positive bacteria and Enterococcus faecalis.

Packaging

5 mL Amber Glass Screw Cap Vial (840520P-1mg)
5 mL Amber Glass Screw Cap Vial (840520P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

No data available

flash_point_c

No data available

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Lucia Palacios et al.
PloS one, 9(4), e93830-e93830 (2014-04-05)
Galloyl catechins, in particular (-)-epicatechin gallate (ECg), have the capacity to abrogate β-lactam resistance in methicillin-resistant strains of Staphylococcus aureus (MRSA); they also prevent biofilm formation, reduce the secretion of a large proportion of the exoproteome and induce profound changes
Staphylococcal phenotypes induced by naturally occurring and synthetic membrane-interactive polyphenolic beta-lactam resistance modifiers
Palacios L, et al.
Testing, 9(4), e93830-e93830 (2014)
Multiple peptide resistance factor (MprF)-mediated resistance of Staphylococcus aureus against antimicrobial peptides coincides with a modulated peptide interaction with artificial membranes comprising lysyl-phosphatidylglycerol
Andra J, et al.
Journal of Biochemistry and Molecular Biology Research, 286(21), 18692-18700 (2011)
Diffraction studies on natural and model lipid bilayers
Sebastiani F, et al.
The European physical journal. C, Particles and fields, 213(1), 355-365 (2012)
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
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