NEW METHODS FOR PREPARATION OF ALPHA & BETA HEXOFURANOSIDES

点击翻译按钮获取中文摘要

These studies are preliminary to synthesizing a variety of furanosides as model compounds for parasite and fungal glycoconjugates that often exhibit non-reducing terminal furanose residues as immunodominant haptens. Simple furanosides can be used in the production and testing of antibodies for serodiagnosis and as substrates for putative glycosyltransferases and glycohydrolases in fungi and parasitic organisms. A method for maximizing the yields of methyl (- and (-hexofuranosides was tested on glucose, mannose, and galactose. So far, five of the six possible furanosides (with the exception of methyl (-glucofuranoside) from these sugars have been synthesized and isolated in pure form. Identities of the products were authenticated by comparison of 1H-NMR spectra at 600 MHz with those published previously. Since the previously published spectra were acquired at 270 MHz, a number of resonances were poorly resolved and/or exhibited non-first-order coupling. Spectra wer e acquired for this work at much higher field (600 MHz), enabling determination of chemical shifts and coupling constants for a number of ring proton resonances not previously reported for these compounds. Work on obtaining methyl (-glucofuranoside in pure form is continuing.