32770-03-9

Upstream product

• 100-51-6 benzyl alcohol 
• 56777-24-3 benzyl (S)-Lactate 
• 22838-58-0 Boc-D-Val-OH 

Downstream Products

• 1271741-87-7 C₂₅H₃₈N₂O₇ 
• 32770-12-0 Boc-(D-Val-Lac-Val-D-Hyv)2-OBzl 
• 126784-72-3 TFA_.D-Val-Lac-Val-D-Hyv-OBzl 
• 32770-05-1 Boc-D-Val-Lac-Val-D-Hyv-OBzl 

Relevant academic research and scientific papers

Membrane-based sensing approaches

Tethered bilayer lipid membranes can be used as model platforms to host membrane proteins or membrane-active peptides, which can act as transducers in sensing applications. Here we present the synthesis and characterization of a valinomycin derivative, a depsipeptide that has been functionalized to serve as a redox probe in a lipid bilayer. In addition, we discuss the influence of the molecular structure of the lipid bilayer on its ability to host proteins. By using electrical impedance techniques as well as neutron scattering experiments, a clear correlation between the packing density of the lipids forming the membrane and its ability to host membrane proteins could be shown. CSIRO 2011.

ISOPROPENYL CHLOROCARBONATE (IPCC) IN AMINO ACID AND PEPTIDE CHEMISTRY: ESTERIFICATION OF N-PROTECTED AMINO ACIDS; APPLICATION TO THE SYNTHESIS OF THE DEPSIPEPTIDE VALINOMYCIN

Esterification of N-protected α-amino acids was achieved via isopropenyl chlorocarbonate (IPCC) activation.In situ alcoholysis of the unstable mixed anhydride intermediate was catalised by 4-(dimethylamino)pyridine (DMAP).Competing isopropenyl ester formation was negligible when using methylene chloride as the solvent.A variety of esters from primary and secondary alcohols were obtained with good yields (60 to 90 percent), and even the more hindered tertiobutyl alcohol gave acceptable yields under more drastic conditions.The improvement in depsipeptide synthetic methodology is illustrated by preparation of the antibiotic valinomycin, using IPCC for ester bond formation, and BOP reagent for peptide coupling and the last-step cyclisation.