Of L-arabinose

Method B (one-pot procedure)-. 5 g (33 mmol) of L-arabinose. 12 mL of ethanol and 4mL (36.7 mmol) of bcnzylaminc arc heated on a steam bath for 5 to 10 min to give a clear solution. After cooling, 2.5 mL of anliyd hydrogen cyanide are added. Spontaneous crystallization of the product begins within a few minutes. After cooling for 2 h with an ice-bath, the product is isolated by filtration and washed with ethanol yield 7.0-7.5g (79-85%) nip 129-131 C after recrystallization from ethanol mp 130-132 C. 

Characteristics of fraction I. The carbohydrate content of Fraction I was 84.4 %, in which the main component is D-galacturonic acid (71 %). Consequently, the polysaccharide is of a pectic type. The neutral sugars accounted for 13.4 % and according to their qualitative composition (Table 2) they correspond to the composition of pectin, isolated from sunflower heads (18). It is worth noting the high content of L-arabinose and D-galactose, compared with the other monosaccharides. The protein content was 7.8 %. 

The galactose, arabinose and xylose transporters of E. coli The bacterium E. coli possesses at least 7 proton-linked, active transport systems for sugars (for a recent review see [212]). Three of these transporters, which catalyze the uptake of L-arabinose, D-xylose and D-galactose by symport with protons, are related in sequence to the sugar transporters discussed above. They probably represent the best-characterized of the non-mammalian transporters, and so are discussed here in some detail. 

D-Lyxose yielded a D-lyxosyl chloride 2,3,4-tri(chlorosulfate) which, on treatment with chloride ion, led to a dichlorodideoxy compound, most probably 2,4-dichloro-2,4-dideoxy-L-arabinose.353 D-Glucose gave a compound presumed to be 4,6-dichloro-4,6-dideoxy-a,/3-D-galactosyl chloride 2,3-di(chlorosulfate),360 and D-xylose afforded a monochloromonodeoxy derivative formulated, on indirect evidence, as 4-chloro-4-deoxy-L-arabinopyranosyl chloride 2,3-di(chlorosulfate).360 3,4-Dichloro-3,4-dideoxy-/3-D-ribopyranosyl chloride 2-(chlorosulfate) was the major, and 4-chloro-4-deoxy-a-D-xylopyranosyl chloride 2,3-di(chlorosulfate) the minor, product from the reaction of L-arabinose with sulfuryl chloride at room temperature for 24 hours.357,361 It has been established that, on reaction with sulfuryl chloride at low temperature, crystalline a-D-xylopyranose and /3-D-lyxopyranose afford, respectively, the 2,4,6-tri(chlorosul-fate)s of /3-D-xylopyranosyl chloride and a-D-lyxopyranosyl chloride,362 363 confirming that substitution at C-l occurs by an Sn2 process on a l-(chlorosulfuric) ester intermediate. 

That the same enzyme,28 sucrose phosphorylase, is involved in the reaction of L-arabinose is indicated by the following observation. When L-arabinose is added to a mixture containing the enzyme, D-glucose-1-phosphate and D-fructose, of which the last is present in insufficient concentration to give the maximum rate of sucrose formation, an increase... 

Other workers140 have also examined the products derived by hydrolysis of periodate-oxidized xylan. Both wheat straw and com cob xylan, after oxidation and hydrolysis, yield small amounts of L-arabinose and D-xylose. These sugars are obtained even after the xylans have been subjected to extended periods of oxidation. It is concluded that the D-xylose constituted branch points in the xylan. Likewise, the L-arabi-nose molecules must not have been terminal units in a xylan chain but must have been either interior units in the xylan molecule or have constituted an araban-like polysaccharide which is in combination or admixture with the xylan polysaccharide. 

The transformation of L-arabinose (58) to lactone 57 was based on a route developed by Marquez and Sharma [51] Selective protection of the primary hydroxy group with TBDPSCl and oxidation of the lactol moiety with bromine afforded lactone 59. Subsequent selective deoxygenation a to the carbonyl group proceeded under Barton-McCombie conditions providing lactone 57 in 21% yield (Scheme 14). 

L-Ribose is quite rare and the only practical method for its preparation is the transformation of L-arabinose by the method of Austin and HumoUer (4 steps, 9.5 % overall yield). L-Ribose has also been derived from, 2,3-<9-isopropylidene-L-glyceraldehyde, (5 steps, 12 %) after separation from a mixture containing L-arabinose. In Scheme 7 we summarize our total syntheses of D- and L-ribose derivatives using the " naked sugars" 32 and 38, respectively." Ketone 138 (Scheme 4) was oxidized into the corresponding lactone (-)-158 with MCPBA in 98 % yield. Treatment with anhydrous methanol, 2,2-dimethoxypropane and a small amount of methanesulfonic acid afforded the methyl 5-deoxy-D-allonate (-)-I59... 

Arabinose isomerase [EC 5.3.1.3] catalyzes the interconversion of D-arabinose and D-ribulose. The enzyme will also utilize L-fucose and more slowly utilize L-galactose and D-altrose as substrates. L-Arabinose isomerase [EC 5.3.1.4] catalyzes the interconversion of L-arabinose and L-ribulose. 

The novel type of disaccharide IX, consisting of a unit of n-galactose joined to a unit of L-arabinose, was obtained by autohydrolysis of gum arabic. The structure of this disaccharide was proved by the fact that methylation yielded the heptamethyl ether X and this gave on hydrolysis 2,3,4,6-tetramethyl-D-galactose (XI) and 2,4-dimethyl-L-arabinose (XII). 

Further experimental evidence is now available which enables the statement to be made that in mesquite gum the side chains of L-arabinose are attached to C3 of some D-galactose residues and to C6 of others. The evidence for this observation is that the degraded mesquite gum,... 

The crude gum tragacanth is a mixture of the salt of a complex acid polysaccharide and a neutral polysaccharide composed principally of L-arabinose residues. Starch is also present in the gum. The acid character of this gum is due to units of D-galacturonic acid and not D-glucuronic acid and it is of interest to note that in its ability to form gels it resembles pectin and the plant mucilages, which also contain D-galacturonic acid. 

Fig. 1 Structure of L-arabinose and compounds obtained from various carbohydrates and dime-done (14) in the Sc -mont catalyzed reaction...

Some workers have performed hydrolyses in an autoclave, but it has been shown that 0.5 M sulfuric acid at 120° degrades 33% of L-arabinose and 22% of D-galactose in two hours.75 Such methods are, therefore, only suitable for qualitative analyses, unless accurate corrections are made. Similarly, 90% formic acid has been found76 to decompose 48% of D-xylose and 36% of D-galactose in 20 hours at 100°. Gas-liquid chromatography has been used to examine the products formed by the acid degradation of sugars.77... 

One of the products of the reaction of L-arabinose with sulfuryl chloride in pyridine was the dimer 3,4-dichloro-2,3,4-trideoxy-/3-D-gZycero-pent-2-enopyranosyl 3,4-dichloro-2,3,4-trideoxy-/3-D-gZycero-pent-2-enopyranoside39 (20) the a,a structure had originally been... 

The quantities of L-arabinose and L-arabinan present in living tissues are relatively small, but L-arabinose residues are widely distributed in heteropolysaccharides and glycoconjugates, constituting one of the components of the middle lamella and cell wall of higher plants. There-... 

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