Monosaccharide anhydrides

The compounds usually known as monosaccharide anhydrides or glycose anhydrides (earlier glycosans ), formation of which involves the anomeric hydroxy group, are named by the same procedure. In these cases the order of preference of ring size designators is pyranose > furanose > septanose. However, three- or four-membered rings should normally be cited as anhydro if there is a choice. 

HPLC-LTQ/FTMS N-Unked glycosylation structures in human plasma HPLC-Ion Trap MS Proteins expressing differences among isolates of Meloidogyne spp. HPLC-MALDI Monosaccharide anhydride levoglucosan, galactosan, and mannosan in the... 

Yttri, K. E., Dye, C., Slordal, L. H., and Braathen, O. A., Quantification of monosaccharide anhydrides by liquid chromatography combined with mass spectrometry Application to aerosol samples from an urban and a suburban site influenced by small-scale wood burning. Journal of the Air and Waste Management Association 55(S), 1169-1177, 2005. 

Saarnio K, Niemi JV, Saarikoski S, Aurela M, Timonen H, Teinila K, Myllynen M, Frey A, Lamberg H, Jokiniemi J, Hillamo R (2012) Using monosaccharide anhydrides to estimate the impact of wood combustion on fine particles in the Helsinki Metropolitan Area. Boreal Environ Res 17 163-183... 

Dye C, Yttri KE (2005) Determination of monosaccharide anhydrides in atmospheric aerosols by use of high-performance liquid chromatography combined with high-resolution mass spectrometry. Anal Chem 77 1853-1858... 

Acetic anhydride, electrostatic potential map of, 791 reaction with alcohols, 807 reaction with amines, 807 reaction with monosaccharides, 988... 

Note 1. Many of the possible conformations are not likely to contribute significantly to the chemistry of a particular monosaccharide, but must be stabilized by formation of additional rings, as in anhydrides or other derivatives. Some others may occur as transition-state intermediates. 

An intramolecular ether (commonly called an intramolecular anhydride), formally arising by elimination of water from two hydroxy groups of a single molecule of a monosaccharide (aldose or ketose) or monosaccharide derivative, is named by attaching the (detachable) prefix anhydro- preceded by a pair of locants identifying the two hydroxy groups involved. 

The cyclic product of condensation of two monosaccharide molecules with the elimination of two molecules of water (commonly called an intermolecular anhydride), is named by placing the word dianhydride after the names of the two parent monosaccharides. When the two parent monosaccharides are different, the one preferred according to the order of preference given in 2-Carb-2.1 is cited first. The position of each anhydride link is indicated by a pair of locants showing the positions of the two hydroxy groups involved the locants relating to one monosaccharide (in a mixed dianhydride, the second monosaccharide named) are primed. Both pairs of locants immediately precede the word dianhydride . 

Bhaskar and Loganathan96 described O-peracetylation of monosaccharides, disaccharides, and methyl glycosides (94) with acetic anhydride under catalysis by acid zeolites. From the panel of zeolites tested (HY, HEMT, HZSM-5, HZSM-12, HZSM-22, and H-beta), the large-pore zeolite H-beta provided the best yields of the fully acetylated sugars, most of them being over 85% and up to 99%, with the pyranose forms 95 accounting for 66-100% of the reaction products (Scheme 22). 

Monosaccharides contain a number of alcoholic hydroxyl groups, and thus can react with acid anhydrides to yield corresponding esters. For example, when glucose is treated with acetic anhydride and pyridine, it forms a pentaacetate. The ester functions in glucopyranose pentaacetate undergo the typical ester reactions. 

The alcohol groups of a monosaccharide can be converted to esters by the methods described in Section 19.4. Thus, the reaction of o-D-gl ucopyranose with acetic anhydride produces a pentaacetate. Note that the hemiacetal hydroxy group is also esterified in this reaction. 

A polar stationary phases such as ODS and TMS and polar such as CN, diol, or NO2 have been successfully applied to the separation of monosaccharides Separation of maltodextrin derivatized with trifluoroacetic anhydride using FID and a CN packed column Capillary supercritical fluid chromatography-MS is well suited to confirm the identity of the TMS derivative of inositol triphosphate Chiral analytes Enantioseparation... 

The OH groups of monosaccharides can also be converted to esters. For example, treatment of P-D-glucose with either acetic anhydride or acetyl chloride in the presence of pyridine (a base) converts all OH groups into acetate esters. 

Most of the acetylated monosaccharides afford the more stable anomeric fluoride in this process. However, the action of a solution of hydrogen fluoride in acetic anhydride on 1,6-anhydro-j8-D-glucopyranose triacetate (1) gave tetra-O-acetyl-jS-D-glucopyranosyl fluoride (3). This result is prob-... 

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