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840520P

Avanti

16:0 Lysyl PG

Avanti Polar Lipids

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

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 Polar Lipids

lipid type

bioactive lipids
phospholipids

shipped in

dry ice

storage temp.

−20°C

Inchi Code

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../s1

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-]

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)

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)
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
Characterization of the mechanisms of daptomycin resistance among Gram-positive bacterial pathogens by multidimensional lipidomics
Hines KM, et al.
mSphere, 2(6), e00492-e00417 (2017)

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