Octyl-P-D-glucopyranoside

Paraformaldehyde fixes by crosslinking surface proteins. Ethanol and methanol work through precipitation of membrane components. Triton X-100 and Tween-20 permeabilize membranes. Other permeabilizers are saponin (0.1-10% [v/v] in PBSG), L-lysophosphatidylcholine, and n-octyl-P-D-glucopyranoside (1-10 pg/mL in water). 

TLC and HPLC. To determine the best solvents for HPLC, 5pl of the C18 concentrated PVP fraction were separated on analytical TLC plates coated with either C18 reversed phase adsorbant or with silica. One cm sections of the plates were removed, placed in buffer, hydrolyzed, extracted and the p-damascenone charm determined. Standards containing 5 mg each of 1 -O-n-octyl- p-D-glucopyranoside and a-methyl-D-mannoside were run simultaneously on the same plate and visualized by spraying with aniline-diphenylamine-acetone-phosphoric acid 80% (4 mL 4 g 200 mL 30 mL) (10). HPLC separations were performed on a 0.46 mm x 25 cm column packed with 5 im C18, eluted with 60/40 methanol water at a flow of 0.8 mL/min. The refractive index of samples was recorded with a Knauer differential refractometer. Fractions were collected every minute and assayed for p-damascenone charm. 

Both groups used intact trimeric PS-I complex, isolated from Synechococcus using either detergent octyl P-D-glucopyranoside " or Triton XI00. Both groups obtained very similar results. We will use the results of Vassiliev et for illustration. When the intact complex ( AB ) was treated with HgCl2... 

After the film is dried under vacuum to remove residual solvent, hydration is performed with 35 mM n-octyl P-D-glucopyranoside (OGP), a nonionic detergent, which is added at a concentration known to cause solubilization of the lipid components used. To ensure that this critical step is complete, the lipid mixture is heated at 50°C in a water bath. 

Patthi, S., et al. (1987). Hydrodynamic Characterization of Vasoactive Intestinal Peptide Receptor Extracted from Rat Lung Membranes in TRITON-X-100 and n-octyl-P-D-glucopyranoside, J. Biol. Chem. 262 15740-15745. 

Muramatsu W, Kawabata T (2007) Regioselective acylation of 6-O-protected octyl p-d-glucopyranosides by DMAP catalysis. Tetrahedron Lett 48 5031-5033... 

Kawabata T, Muramatsu W, Nishio T, Shibata T, Uruno Y, Stragies R (2008) Regioselective acylation of octyl p-d-glucopyranoside by chiral 4-pyrrolidinopyridine analogues. Synthesis 747-753... 

Scheme 1 Leaving group dependence in the DMAP-catalyzed acetylation of octyl p-D-glucopyranoside...

Scheme 3 Acetylation of octyl p-D-glucopyranoside using functionalized DMAP derivatives...

Scheme 4 Top selective monoacylation of octyl p-D-glucopyranoside catalyzed by C2 symmetric PPY derivative 3. Bottom monoacylated pyranosides prepared using catalyst 3...

Scheme 1 Random acylation of octyl P-D-glucopyranoside with DMAP-catalyzed acylation...

Effects of catalyst 4-9 on site-selective acylation of octyl p-D-glucopyranoside in toluene at 20 °C were investigated (Table 1). In reactions catalyzed by DMAP and catalysts 5-7, acylation took place predominantly at the primary C(6)-OH... 

Table 1 Effects of catalysts on site-selectivity in acylation of octyl p d glucopyranoside OH ...

Scheme 6 Synthesis of C(4)-0-acylate of octyl p-D-glucopyranoside by (a) catalyst-controlled site-selective acylation, and (b) conventional protection/deprotection procedure...

Scheme 7 Mechanistic implications, (a) Non-selective acylation of 10 even in the presence of catalyst 8. (b) Competitive acylation between octyl P-D-glucopyranoside and 2-phenylethanol catalyzed by 8...

Fig. 3 A proposed transition state assembly for site-selective acylation of octyl p-D-glucopyranoside promoted by catalyst 8...

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