Glutaric acid, structure

Glutaric acid, structure of, 753 Glutathione, function of. 668 prostaglandin biosynthesis and, 1070... 

Structure 187 was proposed for deoxodihydroleontalbinine. Leontalbinine perchlorate could not be reduced, while deoxoleontalbinine perchlorate was reduced by sodium borohydride. This suggested an a,p position of the double bond with respect to the amine nitrogen, which was confirmed by oxidation to glutaric acid, probably via the intermediate product 189 (Scheme 34). Since structure 188 proposed for leontalbinine is correct, structure 187 given to deoxodihydroleontalbinine is incorrect and has to be changed to 190. 

Similar structures have been found for many other dicarboxylic acids, including succinic acid, COOH(CH ) COOH glutaric acid, COOH(CH ) COOH adipic acid, COOH(CH,) pOOH, and sebacic aoid, COOH(CH )jCOOH. Crystal structure determinations have also been made of many carboxylic acid hydrates in all of the crystals the carboxyl groups form hydrogen bonds, usually with water mole oules. An example is oxalic acid dihydrate in this crystal the 0—H 0 distance is 2.50 A. 

Figure 8.1 Crystal structure of zinc glutarate prepared from ZnO and glutaric acid in toluene. Structure determined from X-ray powder pattern (view along the c-axis) [12].

Figure 11.26 X-ray crystal structure of the 2 2 complex of 11.41 with glutaric acid showing the matching of the guest and host hydrogen-bonding binding sites.37...

Figure 12 Molecular structures of four bischelating ligands commonly used to form octahedral Ru- and Rh-complexes for attachment to DNA phenanthrenequinone diimine (phi), dipyridophenazine (dppz), 5-(amido-glutaric acid)-l,10-phenanthroline (phen ), and 2,2 -bipyridine (bpy).

Figure 7.7. Chemical structures of iminodiacetic acid—glycerol prepolymers (A), and diacid—glycerol prepolymers (B). Note n = 2 for succinic acid, n = 3 for glutaric acid, and n = 7 for azelaic acid.

This conclusion was strengthened by the preparation of two different fully methylated cymaronic lactones. Cymarose was oxidized to cymaronic lactone, which was then methylated to give 5-methyl-cy-maronic lactone (1,4) (XLII), a sirup which was characterized by the phenylhydrazide of the corresponding acid. On the other hand, methyl cymaropyranoside was completely methylated to methyl 4-methyl-cymaropyranoside. The latter, after hydrolysis of the glycosidic methyl group and oxidation, yielded 4-methylcymaronic lactone (1,5) (XLIII), also a sirup, but which differed in rotation from the 1,4-lactone and formed a different phenylhydrazide. Further, the assignment of a 1,5 structure to XLIII was supported by the formation of a dimethoxy-glutaric acid on oxidation of XLIII with nitric acid. 

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