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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

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

SMILES string

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

General description

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

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.

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_germany

WGK 3

flash_point_f

No data available

flash_point_c

No data available

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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
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)
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
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