Arabinitol, 1,5-dideoxy

The latter were further converted in one step to l,4-dideoxy-l,4-imino-D-arabinitol [(2R,3 A,4A)-3,4-dihydroxy-2-(hydroxymethyl (pyrrolidine] and fagomine (l,2,5-trideoxy-l,5-iminohexitol), respectively, by palladium-catalyzed hydration23 27. These compounds are extremely efficient inhibitors of glycosidases24. 

Jamali, B., and Nielsen, H. M. (2003). Development and validation of a capillary electrophoresis-indirect photometric detection method for the determination of the non-UV-absorbing 1,4-dideoxy-l,4-imino-d-arabinitol in active pharmaceutical ingredients, solutions and tablets using an internal standard. J. Chromatogr. A 996(1—2), 213-223. 

In 1985, l,4-dideoxy-l,4-imino-D-arabinitol (14) was independently discovered in a legume, Angylocalyx boutiqueanus39 and a fem, Arachniodes standishii40... 

Selected from among their contributions were the first example of a synthetic furanoid iminoalditol, l,4-dideoxy-l,4-imino-D-mannitol (19, Scheme 7) 49 the first synthesis of the powerful L-fucosidase inhibitor l,5-dideoxy-l,5-imino-L-fucitol (20),50 the synthesis and structure confirmation of l,4-dideoxy-l,4-imino-D-arabinitol... 

The synthesis of l,5-dideoxy-l,5-imino-L-arabinitol (13), a derivative of (5) lacking the hydroxymethyl side chain at C-5 was reported [49]. This compound did not exhibit any appreciable activity with imspecified galactosidases. 

Bols and co-workers [61] synthesized isofagomine (23), a compound in which the basic hetero-atom replaces the anomeric carbon, and showed that this new type of synthetic sugar analogue is one of the strongest inhibitors of -glucosi-dase from almonds known to date. Following this innovative work, Ichikawa and Ichikawa prepared (3i ,4 ,511)-3(] )-hydroxymethylpiperidine (l,5-dideoxy-2-C-hydroxymethyl-l,5-imino-D-arabinitol, 24) [62] from D-lyxose. This was... 

An amidrazone (58) derived from 5-amino-5-deoxy-L-fuconolactam was found to inhibit a recombinant human a-L-fucosidase with a K -value of 820 nmol/1 [ 111 ]. A simple synthesis of 1,5-dideoxy-1,5-imino-D-arabinitol (59), previously prepared by Ganem et al. [49] as a potential maimosidase inhibitor, was applied to the affinity purification of a-L-fucosidase from bovine kidney by an improved method and the characterization of the enzyme thus obtained [112]. The relatively low affinity of this compound to the enzyme (Kj 2.2 pmol/1 at pH 7) compared to 1-deoxyfuconoJirimycin (51) turned out to be advantageous in terms of enzyme recovery and yield. Structurally related, suitably protected 5-amino-5-deoxy-D-arabinopyranose (60), was coupled with a N-acetyl-6-deoxy-6-thio-D-glucosaminide (61) to give a stable thioglycoside (62) [113]. 

The formation of 34 was explained by a rearrangement of 33 by way of a benzoxonium intermediate the ion is attacked at the less-hindered, C-5 position, to give a 5-deoxy-5-iodo derivative. The structure of 34 was confirmed by its reduction to 4-0-benzoyl-l,5-dideoxy-2,3-0-iso-propylidene-L-arabinitol. 

For a long time, this reaction was conducted exclusively with acety-lated nitriles of aldonic acids, and the products obtained were known in general as "aldose-amides. Fischer2 used this reaction to transform tetra-O-acetyl-L-rhamnononitrile into l,l-bis(acetamido)-l,5-dideoxy-L-arabinitol, whose subsequent hydrolysis and oxidation allowed him to determine the configuration of dextro-tartaric acid (L-threaric acid). 

Acetamido-5-deoxy-D-threo-pentulose and 5-acetamido-5-deoxy-L-erythro-pentulose (204) are obtainable by the bacterial oxidation of 1-acetamido-l-deoxy-D-arabinitol and 1-acetamido-l-deoxy-D-ribitol, respectively. Both ketoses are crystalline, and show a strong carbonyl vibration in their infrared spectra. Accordingly, they exist in the acyclic form. Their isopropylidene acetals are likewise acyclic. Furthermore, 5-acetamido-5,6-dideoxy-L-xylo-hexulose (205), obtainable by bacterial oxidation, shows a great tendency to assume the acyclic structure. 5-Acetamido-5-deoxy-L-xi/io-hexulose (206) may be obtained by the bacterial oxidation of 2-acetamido-2-deoxy-D-glucitol it assumes, exclusively, the sterically more-favored pyranose form. ... 

Dideoxy-l, 4-imino-(2-0-P-D-elucopYranosyl)-D-arabinitol Moms bombycis (Moraceae) leayes Moms alba (Moraceae) roots ... 

Of these, 67, the N-hydroxyethyl derivative of compound 2, exhibited suitable properties and has been marketed against noninsulin-dependent diabetes as Miglitol [180]. Similarly, Emiglitate 68 and the disaccharide mimetic MDL 73945 69 show promising antidiabetic activities [181]. Other compounds such as l,4-dideoxy-l,4-imino-D-arabinitol 60 have also been put forward as possible drug candidates in this context [159]. 

Hung, R R, Straub, J A, Whitesides, G M, a-Amino aldehyde equivalents as substrates for rabbit muscle aldolase s3mthesis of l,4-dideoxy-l,4-imino-D-arabinitol and 2(R),5(R)-bis(hydroxy-methyl)-3(R),4(R)-dihydrox3fpyrrolidine, J. Org. Chem., 56, 3849-3855, 1991. 

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