Rapid glycosylations under extremely mild acidic conditions. Use of ammonium salts to activate glycosyl phosphites via P-protonation

Trifluoromethanesulfonic acid salts of tertiary amines were employed as extremely mild acidic activators for rapid glycosylations. Glycosyl phosphite triesters bearing an acid-labile 4,4′-dimethoxytrityl (DMTr) group for transient protection worked as glycosyl donors effectively in the presence of the activators to afford the corresponding disaccharides in good yields without loss of the DMTr group.     

Analysis of ligand-independent cap formation induced in hypertonic medium

Ligand-independent (LI-) cap formation induced in hypertonic medium was investigated particularly in comparison with ligand-dependent (LD-) cap formation. Major observations presented in this report are:

1. 1. Two species of receptors moved differentially on individual lymphocytes during LI-cap formation.

2. 2. Bipolar cap was formed in a minor population of the total cells after incubation in 2 x PBS in the absence of ligand whereas no bipolar cap was obtained in the presence of ligand in 2 x PBS.

3. 3. LI-cap formation was induced repeatedly on the cells that had formed cap when exposed to 2 x PBS for the first time and had regained diffuse distribution of receptors by lowering the osmolarity of medium to PBS.

4. 4. Maintenance of the cap-state in 2 x PBS in the absence of ligand requires cellular functions which are inhibitable either by sodium azide or by cytochalasin B (CB).

5. 5. Specific binding of antibodies directed against immunoglobulin to B lymphocytes stimulates LI-cap formation of unrelated receptors on these cells.

Although some essential features of LI-cap formation (e.g. independency of ligand and accumulation of microvilli in the region of cap) are clearly distinguishable from those of LD-cap formation, it can be pointed out from the present results that LI-cap formation appears to be similar in part to LD-cap formation of concanavalin A (ConA) receptors rather than to LD-cap formation of surface Ig in regard to its features such as the reversibility of cap formation. These results are discussed in terms of interactions between surface receptors and cytoplasmic structures.     

Metabolism of 3-deoxyglucosone,an intermediate compound in the Maillard reaction,administered orally or intravenously to rats

Tha Amadori rearrangement compound, the product in the early step of the Maillard reaction of proteins with glucose, is known to be degraded into 3-deoxyglucosone (3DG), a 2-oxoaldehyde. In order to elucidate the metabolic pathway of 3DG, [¹⁴C]3DG was synthesized from [¹⁴C]-glucose and administered to rats orally and intravenously. 2 h after oral administration of [¹⁴C]3DG, the percentages of radioactivity (RaI%) in stomach, small intestine and urine were 3.9, 60 and 6.4%, respectively, while RaI% in liver, kidney, spleen, blood and CO₂ were less than 0.5%. The absorption rate of 3DG was obviously lower in comparison with that of glucose. 3 h after intravenous administration of [¹⁴C]3DG, the RaI% in urine was 72% and those in liver, kidney, spleen, blood and CO₂ were less than 1%. It therefore appeared that the absorbed 3DG was not biologically utilized by the rats, but was rapidly excreted in the urine. Some metabolites of [¹⁴C]3DG were detected in urine by TLC-autoradiography. The main metabolite was purified and identified as 3-deoxyfructose by FD-MS and ¹³C-NMR spectroscopy, indicating that the aldehyde group of 3DG was reduced to an alcohol.     

Fragmenting oligochaete Enchytraeus japonensis: A new material for regeneration study

Enchytraeus japonensis, a recently described terrestrial oligochaete, reproduces asexually by fragmentation and subsequent regeneration. Taking notice of its high potential as a new material for regeneration study, detailed studies were undertaken on the regeneration and reproduction of E. japonensis. The full-grown body divided into 6-13 fragments that regenerated into complete individuals in 4 days, grew to full length in 10 days, and then fragmented again. Regeneration of the head and tail was epimorphic, involving blastema formation, while old segments in the regenerating fragment morphallactically transformed into the appropriate segments to retain the proper body proportions, which could be visualized by histochemistry for alkaline phosphatase. Artificially cut fragments regenerated either normally or into dicephalic monsters with biaxial heads depending on the conditions. Fragmentation could be induced by decapitation, and sexual reproduction was also found inducible in the laboratory. These findings, together with its simple metameric morphology and ease of culture and handling, suggest that E. japonensis is an excellent material for studying animal regeneration.     

Construction of a Quantitative Three-dimensional Model for Odor Quality using Comparative Molecular Field Analysis (CoMFA)

A quantitative structure-activity relationship (QSAR) studyof odorants was performed taking an odor as an activity. Asan example, we took the ‘green odor of pyrazine derivatives’as an activity. Conformational analysis of the pyrazine derivativeswas performed, and conformers were selected using the longestside-length of a circumscribed box (LLCB) as a criterion. Comparativemolecular field analysis (CoMFA) was used to elucidate the three-dimensional(3D) structural features of the derivatives. As a result, itwas found that the steric and electrostatic features of thederivatives were correlated with human olfactory detection thresholdvalues. We constructed a quantitative 3D model using the graphicviews of CoMFA and partial structures of the derivatives. Theprediction of human olfactory detection threshold values ofother pyrazine derivatives with green odor was possible by usingthe 3D model. As another example, we took the ‘sweet odorof compounds with various structures’ as an activity.A quantitative 3D model for sweet odor was constructed in thesame manner. Analysing the structural features of odorants byCoMFA and constructing 3D models for several important odorqualities would help to (i) explain or predict human olfactorydetection threshold values of interesting odorants, (ii) designnew odorants by suggesting the steric and electrostatic requirements,and (iii) elucidate the mechanism of odorant-receptor interaction.Chem Senses 21: 201–210, 1996.     

Effects of total submergence in saltwater on growth and leaf ion content of preflooded and unflooded Taxodium distichum saplings

Preconditioning by hypoxic condition would contribute higher tolerance to anoxic condition in physiological and metabolic aspects of various plant species. In expectation of improvement of salinity tolerance, effects of preconditioning with soil flooding on growth responses and photosynthetic activity in relation to Na⁺ content in leaves and roots were studied using 2-year-old Taxodium distichum saplings. A submergence experiment was performed at three salt concentrations (0, 4000, and 8000 ppm NaCl), and preconditioning was started 2 months prior to the beginning of submergence treatments. Continuous soil flooding with freshwater as a control did not inhibit growth in height and stimulated diameter increment of the saplings. Saplings submerged in saltwater and freshwater also showed no morphological changes during submergence treatments. However, leaf injury and shoot dieback were observed in drained saplings that had been submerged in saltwater. Na⁺ and K⁺ ion contents increased with increases in salt concentration in both preconditioned and unconditioned saplings, whereas ion contents in preconditioned saplings tended to be higher than those of unconditioned saplings.     

Morphological Features of a Filamentous Phage of Vibrio cholerae O139 Bengal

A filamentous phage was isolated from carrier strain AI-1841 of Vibrio cholerae O139 Bengal and thus was termed fs phage. The phage was measured to be approximately 1 μm in length and 6 nm in width. One end of the phage was slightly tapered and had a fibrous appendage. The plaques developed on strain AI-4450 of V. cholerae O139 were small and turbid. The phage grew in strain AI-4450 and reached a size of 10⁸ to 10⁹ pfu/ml at 5 hr after infection without inducing any lysis of the host bacteria. The group of phages attached on rod-shaped materials like fimbriae of this bacteria, with their fibrous appendages at the pointed end, were often found in the phage-infected culture. The anti-fimbrial serum effectively inhibited the infection of fs phage to the host strain AI-4450. We thus concluded that the phage can be adsorbed on fimbriae with a fibrous appendage on the pointed end of the phage filament.