Hexoses structure

Monosaccharides have the formula (CH2 0) , where n is between 3 and 6. Of the 70 or so monosaccharides that are known, 20 occur in nature. The most important naturally occurring monosaccharides contain five carbons (pentoses) or six carbons (hexoses). Structures of ribose, an important pentose, and a-glucose, a hexose that is the most common monosaccharide, are shown in Figure 13-14. As shown in the figure, it is customary to number the carbon atoms in a monosaccharide, beginning with the HCOH group adjacent to the ether linkage. 

Proton and C-NMR data compare well with each other and suggest that surface ocean HMWDOM has a H C ratio of approximately 1.8—1.9 (Aluwihare, 1999 Benner et al, 1992) and an 0 C ratio between 1 and 1.1. These H C and 0 C ratios are very close to those of a pure carbohydrate with a general hexose structure (e.g., C6H12O6). In comparison, humic substances isolated from seawater have an H C ratio between 1.2 (direct elemental analyses) and 1.4 (based on NMR estimates) and are therefore, relatively C-rich (Hedges et al, 1992). The H C and 0 C composition of phytoplankton as estimated by NMR spectroscopy is approximately 1.7 and 0.3, respectively (Hedges et al, 2002). In comparison to phytoplankton... 

Glucose is a six-carbon aldohexose. The straight chain hexose structures can become cyclic. When aldehydes and ketones undergo reactions with alcohols, hemiacetals or hemiketals are formed. In aldohexoses, the eyclic structure is formed when the hydroxyl group in the fifth carbon reacts (nucleophilic addition) with the carbonyl carbon of the aldehyde group. The product formed is a hemiacetal. The cyclization is represented in Figure 29-4. 

Fischer contemplated the problem and reasoned that D-glucaric acid could be obtained by nitric acid oxidation of two different hexoses, structure M above... 

The four kelohexoses are fructose, sorbose, allulose and tagatose. See glucose for example of isomerization between open chain and cyclic structures in a typical hexose molecule. 

Properties and Structure. a -Acid glycoprotein (a -AGP) has a molecular mass of about 41,000 and consists of a peptide chain having 181 amino acid residues and five carbohydrate units (14,15). Two cystine disulfide cross-linkages connect residues 5 and 147 and residues 72 and 164. The carbohydrate units comprise 45% of the molecule and contain siaUc acid, hexosamine, and neutral hexoses. In phosphate buffer the isoelectric point of the... 

The bromide (5) failed to couple with dialkoxypyrimidines, even at elevated temperatures the failure is probably because of steric conditions imposed by the axially oriented C-4 p-nitrobenzoyloxyl group (see structure 5) this same group in the other halides (la, lb, 2a, 2b, 4a, and 4b) discussed in the foregoing is an equatorial substituent. Accordingly, the preparation of a differently constituted halide of 2-deoxy-D-Zt/xo-hexose is being investigated for the synthesis of pyrimidine nucleosides. 

The six-membered ring of a hexose such as a-glucose takes on a puckered structure. A molecular plane can be defined that passes through the midpoints of all the bonds of the ring. Bonds to non-ring atoms are either perpendicular to this plane (shown in green) or roughly parallel to the plane (shown in brown). 

Hexose monosaccharides can form both five- and six-membered rings. In most cases, the six-membered ring structure is more stable, but fructose is an important example of a hexose that is more stable as a five-membered ring. The structure ofy6-fhictose is shown in Figure 13-17. Notice that there are — CH2 OH fragments bonded to two positions of this five-membered ring. Examples and explore the structures of monosaccharides in more detail. 

Although the chemical formulas indicate that ribose is a pentose and fructose is a hexose, the ring portions of the structures are the same size. Proceeding clockwise around the rings from the oxygen atom, we see that the structures differ at the first two positions. In the first position, ribose has a carbon atom bonded to —H and —OH, while)S-fructose has a carbon bonded to —OH and — CH2 OH. In the second position the molecules have the same two bonds but in different orientations. The OH group points up in y6-fructose and down in ribose. The two molecules have the same structures at the other positions. 

B. Hexoses.—Muramic acid 6-phosphate (63), which occurs in the cell walls of bacteria, has now been synthesised, thus confirming the structure of this acid-stable compound. 

Glutathione reductase (GR) catalyzes the reduction of oxidized glutathione (GSSG) to reduced glutathione (GSH) using NADPH provided from the hexose monophosphate pathway. GR, a ubiquitous flavoenzyme, maintains a high value of two for the GSH/GSSG ratio in the red blood cells. l,3-Bis(2-chloroethyl)-nitrosourea (BCNU) selectively inhibits cellular GR. GR is composed of two identical subunits, each of molecular mass 50 kDa (S8). The three-dimensional structure and mechanism of catalysis have been established for human GR (K17). 

Alternatively, if we suppose that the hexose polysaccharide is produced first and is then transformed into pectic acid and araban, at least two types of galactan, other than the one already isolated from pectic materials, would be required to account for the types of structure present respectively in pectic acid and araban. This would seem to be somewhat unlikely since, on this view, one would expect to encounter other types of pectic acid and araban, whereas on the evidence now available the pectic acid isolated from all samples of pectic materials examined appears to be the same, and a similar conclusion applies in the case of the araban. 

The failure of a compound to undergo periodate oxidation can not be regarded as positive proof that it contains no 1,2-glycol structures. If the glycol is securely locked in a trans position, oxidation has been shown not to occur. This resistance has been encountered in the bicyclic anhydro hexoses, for example, l,6-anhydro-/3-D-glucofuranoseM and 1,6-anhydro-a-D-galactofuranose.54 This work has already been summarized in this... 

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