Ribosides, arsenic containing

A number of arsenic-containing ribosides, also referred to here simply as arsenosugars, occur in marine samples. Most of the arsenosugars are dimethylarsinoylribosides (Fig. 2, compounds 9 to 25). This group of compounds was unknown prior to 1981, when 9 and 12 were isolated from a brown alga (55). Structures for the two compounds were origi-... 

Figure 6.58 Representative arsenic-containing ribosides and the proposed biosynthetic C-As bond-making step.

Arsenosugars (arsenic-containing ribosides) As-sugar A, B, etc. See Figure 6.1... 

KA Francesconi, W Goessler, S Panutrakul, KJ Irgolic. A novel arsenic containing riboside (arsenosugar) in three species of gastropod. Sci Total Environ 221 139-148, 1998. 

Treatment of l,2-0-isopropylidene-3,5-di-0-tosyl-a-D-xylofuranose with lithium diphenylarsinide has afforded 5-deoxy-l,2-0-isopropylidene-5-C-diphenylarsino-3-O-tosyl-a-D-xylofuranose, and the arsenic containing ribosides 19 have been prepared using standard procedures. ... 

The chemistry and biology of teniposide, which contains the thio-phen acetal (54) of glucose, has been reviewed.Arsenic-containing ribosides are mentioned in Chapters 17 and 22. 

Inorganic Derivatives.- 1,6-Anhydro 2-chloro-2,4-dideoxy-4-(diphenylphosphoryl)-P-D-glucopyranose, the P-in-the-ring sugar analogues (27) and (28)," the natural arsenic-containing riboside (29), methyl 4,6-0-benzylidene-3-deoxy-3-C-triphenylstannyl-a-D-altropyranoside, two isomeric chromium(III) complexes with 1,3,5-triamino-1,3,5-trideoxy-cw-inositol in the one structure, the vanadium(in) complex (30),and the platinum(Il)-dithiocarbamate complex (31). ... 

Arsenobetaine 54 was present in the extracts of the earthworm, Lumbricus terrestris, as a minor constituent and traces of dimethylarsinic acid 47, ribosides 56, and 57 were also detected [156]. The major arsenic compound in the earthworm extracts was an arsenic-containing... 

McAdam, D.P., Perera, A.M.A., and Stick, R.V. (1987) The synthesis of (R)-2 3 -dihydroxy-propyl-5-deoxy-5-dimethylarsinyl- 3-D-riboside, a naturally occurring arsenic-containing carbohydrate. Aust. J. Chem., 40, 1901-1908. 

The hydrothermal vent shrimp, Rimicuris exoculata, which is known to be a primary consumer of the chemolithoautotrophic bacteria, contained 13 pg/g of arsenic almost exclusively as arsenobetaine 54. The major parts of the extractable arsenic species in the adductor muscle/mantle tissues and in the gill were present as riboside derivatives 56 and 57, while 54 was present at 16% and 3.6%, respectively, in these tissues... 

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