Reactivity of melezitose and raffinose under Mitsunobu reaction conditions

One‐Pot Conversions of Raffinose into Furfural Derivatives and Sugar Alcohols by Using Heterogeneous Catalysts

“…The sequential reactions were confirmed by measuring a time course for the formation of DFF by the successive addition of Amberlyst-15, HT, and Ru/HT into the solution (Figure 4). The Ru/HT catalyst also exhibited good activities for the hydrogenation of fructose, glucose, and galactose into the corresponding sugar alcohols (Table 3, entries [10][11][12]. The achieved 27 % yield of DFF from raffinose was also comparable to that obtained from glucose (25 %), as reported in our previous paper.…”

“…The use of biorenewable resources allows the exploration of opportunities that will partly contribute to secure the domestic supply of energy, support agricultural economics, and produce energy from renewable resources in a carbon-neutral way. [7][8][9][10] Recently, raffinose has gained interest as a potential excipient in stabilizing biomolecules because its specific stabilizing properties are reported to be superior to other sugars, such as lactose, maltose, and sucrose. [5] Raffinose (O-a-d-galactopyranosyl-(1!6)-O-a-d-glucopyranosyl-(1$2)-O-b-d-fructofuranoside) is a naturally occurring indigestible trisaccharide [6] that is composed of galactose, glucose, and fructose sugar units (see Scheme 1) and is one of the most abundant oligosaccharides found in plants and agricultural products, such as beet molasses, sugar cane, honey, eucalyptus manna, cottonseed meal, leaves of the yew, potatoes, grapes, and the seeds of many leguminous plants.…”

“…[5] Raffinose (O-a-d-galactopyranosyl-(1!6)-O-a-d-glucopyranosyl-(1$2)-O-b-d-fructofuranoside) is a naturally occurring indigestible trisaccharide [6] that is composed of galactose, glucose, and fructose sugar units (see Scheme 1) and is one of the most abundant oligosaccharides found in plants and agricultural products, such as beet molasses, sugar cane, honey, eucalyptus manna, cottonseed meal, leaves of the yew, potatoes, grapes, and the seeds of many leguminous plants. [7][8][9][10] Recently, raffinose has gained interest as a potential excipient in stabilizing biomolecules because its specific stabilizing properties are reported to be superior to other sugars, such as lactose, maltose, and sucrose. [11] Raffinose can be completely converted into three hexoses, namely, galactose, glucose, and fructose, through hydrolysis, which are economical and suitable for use as chemical feedstocks (Scheme 1).…”

Synthesis of raffinose by transfructosylation using recombinant levansucrase from Clostridium arbustiSL206

“…The chemical shifts of 13 C NMR spectra for the produced compound are listed in Table . The chemical shifts were compared to previously reported results of raffinose production . The 13 C NMR spectrum revealed 18 carbons with three anomeric carbons ( δ C , 103.765, 98.454, and 92.075 ppm) (Fig.…”

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

“…Reports of Mitsunobu reactions of secondary alcohols in fully functionalized carbohydrates are much scarcer. Rather, reports exist of failed attempts at Mitsunobu reactions of secondary carbohydrate alcohols [23] or the selective functionalisation of primary carbohydrate alcohols in the presence of secondary alcohols [24]. Some examples of successful reactions do exist, though, for oxygen, nitrogen and sulfur nucleophiles [25–28].…”