D Sugar

The rules previously mentioned for assignment of a- and /3-configurations can be readily applied to Haworth projection formulas. For the D-sugars, the anomeric hydroxyl group is below the ring in the a-anomer and above the ring in the /3-anomer. For L-sugars, the opposite relationship holds. 

Assay results with the two new 1,2-cis (ft-d) cardenolides show enhanced activity as compared with the two unnatural, a-D-rhamnosides. They have potencies that fall well within the range for those of the naturally occurring cardenolides. These results support the postulate that the a-D-glycosidic linkage in cardenolides containing D-sugars is unfavorable for cardiotonic activity. 

Figure 25.2 Some naturally occurring D sugars. The -OF group at the chirality center farthest from the carbonyl group has the same configuration as

How many aldoheptoses are there How many are d sugars, and how many are l sriga rs ... 

Fischer projection, 975-978 carbohydrates and, 977-978 D sugars, 980 i., sugars, 980-981 rotation of, 976 R.S configuration of, 977 conventions for, 975-976 Fishhook arrow, radical reactions and, 139, 240... 

Three 3-amino-3,6-dideoxyhexoses, having the d- and L gluco and D-ga-lacto configurations, have been found. The two D-sugars are not very common, but occur in some 0-antigens for example, those from E. coli 0114 (Ref. 60) and E. coli 02 (Ref 61), respectively. The D-galacto isomer has also been found in the cell-wall polysaccharide from Eubacterium saburreum strain L13.3-Amino-3,6-dideoxy-L-glucose has been found in the core part of the Aeromonas hydrophila chemotype 111 LPS. 

As discussed in Chap. 6, nucleic acids contain D-ribose or D-deoxyribose. The corresponding L-form is banished from the information carriers RNA and DNA. So the question is why L-amino acids and D-sugars and not the opposite Two hypotheses are at the fore in this scientific discussion ... 

The question also arises as to where the chiral molecules came from. Were the L-amino acids or the D-sugars selected on the primeval Earth, or are exuaterresuial sources responsible for the homochirality This second possibility is dealt with by hypotheses on the effect of circularly polarised light, of extraterrestrial origin, on chiral molecules in the molecular clouds from which the solar system was formed. One such hypothesis was proposed by Rubenstein et al. (1983) and developed further by others, particularly A. W. Bonner (Bonner and Rubenstein, 1987) both scientists worked at Stanford University. The authors believe that the actual radiation source was synchrotron radiation from supernovae. The excess of one enantiomeric form generated by this irradiation process would have needed to be transported to Earth by comets and meteorites, probably during the bombardment phase around 4.2-3.8 billion years ago. 

Aldose sugars make up a large part of the carbohydrate family, but the ones that are really worth knowing are part of the D-family. The simplest of these D-sugars is the triose glyceraldehyde. From there you have 2 tetroses, 4 pentoses, and 8 hexoses. Each of these aldose sugars has an enantiomer. 

The first such case was concerned with the limited substrate acceptance of d-2-keto-3-deoxy-6-phospho-gluconate (KDPG) aldolase (161). This catalyzes the (reversible) reaction of pyruvate (41) to certain chiral aldehydes such as 42, with formation of aldol products such as 43. It was known that this aldolase is highly specific for chir l-phosphorylated aldehydes with the d configuration at the C2 position leading stereoselectively to a precursor of the corresponding d sugar such as 44 (162) ... 

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