228862-97-3

Usage

Uses

Used in Pharmaceutical Industry:
1-AMINO-2,5-ANHYDRO-1-DEOXY-D-MANNITOL is used as a pharmaceutical compound for its potential role in the treatment of African sleeping sickness. As a substrate for the hexose transporter of Trypanosoma brucei, it can be utilized in the development of drugs targeting this specific parasite, offering a novel approach to combat the disease.
Used in Research and Development:
In the field of research and development, 1-AMINO-2,5-ANHYDRO-1-DEOXY-D-MANNITOL serves as a valuable tool for studying the differences between human and Trypanosoma brucei transport mechanisms. This knowledge can lead to the discovery of new therapeutic strategies and a better understanding of the underlying biology of the disease.
Used in Chemical Synthesis:
Due to its unique chemical properties as a light brown oil, 1-AMINO-2,5-ANHYDRO-1-DEOXY-D-MANNITOL can be employed as an intermediate in the synthesis of various chemical compounds. Its versatility in chemical reactions makes it a valuable asset in the development of new pharmaceuticals, materials, and other applications in the chemical industry.

InChI:InChI=1/C6H13NO4/c7-1-3-5(9)6(10)4(2-8)11-3/h3-6,8-10H,1-2,7H2/t3-,4-,5+,6?/m1/s1

Upstream product

• 127676-61-3 2,5-anhydro-D-mannose oxime 
• 243469-61-6 2,5-anhydro-1-azido-1-deoxy-D-mannitol 
• 229971-49-7 2,5-anhydro-1-benzylamino-1-deoxy-D-mannitol 
• 229016-22-2 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(aminomethyl)tetrahydrofuran-3,4-diyl diacetate 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 84447-04-1 2,5-anhydro-1-O-(p-tolylsulfonyl)-D-mannitol 
• 41107-82-8 2,5-anhydro-D-mannitol 
• 495-75-0 2,5-anhydro-D-mannose 
• 228862-96-2 1-C-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)methanal oxime acetate 

Relevant academic research and scientific papers

Targeting of glut5 for transporter-mediated drug-delivery is contingent upon substrate hydrophilicity

Specific link between high fructose uptake and cancer development and progression highlighted fructose transporters as potential means to achieve GLUT-mediated discrimination between normal and cancer cells. The gained expression of fructose-specific transporter GLUT5 in various cancers offers a possibility for developing cancer-specific imaging and bioactive agents. Herein, we explore the feasibility of delivering a bioactive agent through cancer-relevant fructose-specific transporter GLUT5. We employed specific targeting of GLUT5 by 2,5-anhydro-D-mannitol and investigated several drug conjugates for their ability to induce cancer-specific cytotoxicity. The proof-of-concept analysis was carried out for conjugates of chlorambucil (CLB) in GLUT5-positive breast cancer cells and normal breast cells. The cytotoxicity of conjugates was assessed over 24 h and 48 h, and significant dependence between cancer-selectivity and conjugate size was observed. The differences were found to relate to the loss of GLUT5-mediated uptake upon increased conjugate size and hydrophobicity. The findings provide information on the substrate tolerance of GLUT5 and highlight the importance of maintaining appropriate hydrophilicity for GLUT-mediated delivery.

Flow synthesis of a versatile fructosamine mimic and quenching studies of a fructose transport probe

We describe the synthesis of 1-amino-2,5-anhydro-D-mannose ("mannitolamine"), a key intermediate to the 7-nitro-1,2,3- benzadiazole conjugate (NBDM), using commercially available fluidic devices to increase the throughput. The approach is the first example of a flow-based Tiffeneau-Demjanov rearrangement. Performing this step in flow enables a ～64-fold throughput enhancement relative to batch. The flow process enables the synthesis to be accomplished three times faster than the comparable batch route. The high throughput enabled the production of larger quantities of the fluorescent fructose transport probe NBDM, enabling us to measure key photophysical properties that will facilitate future uptake studies.

Synthesis of C-(D-glycopyranosyl)ethylamines and C-(D-glycofuranosyl)methylamines as potential glycosidase inhibitors

The C-glucosyl aldehyde, 2-C-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal was prepared from the C-glucopyranosyl propene precursor by ozonolysis. Reductive amination of the C-glucosyl aldehyde and subsequent deprotection gave 1-anilino-2-C-(α-D-glucopyranosyl)ethane. The E and Z isomers of the oxime derivative, 1-C-(α-D-arabinofuranosyl)methanal oxime were prepared by treating their aldehyde precursor with hydroxylamine. Acetylation of the oxime, followed by catalytic hydrogenation and deprotection, gave the corresponding 1-C-(α-D-arabinofuranosyl)methylamine. Reductive amination of ethyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside using aniline gave ethyl 5-anilino-5-deoxy-D-lyxo-furanoside. Inhibition studies with these compounds on β-D-glucosidase from sweet almond, using o-nitrophenyl D-glucopyranoside as substrate, were carried out. Copyright (C) 1999 Elsevier Science Ltd.

An easy stereospecific synthesis of 1-amino-2,5-anhydro-1-deoxy-D-mannitol and arylamino derivatives

1-Amino-2,5-anhydro-1-deoxy-D-mannitol and a series of arylamino derivatives were prepared by nitrous acid deamination of 2-amino-2-deoxy-D-glucose and subsequent reductive amination of the resulting 2,5-anhydro-D-mannose. Some of these compounds showed a

Ethambutol-sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis

Ethambutol is an established front-line agent for the treatment of tuberculosis, and is also active against Mycobacterium avium infection. However, this agent exhibits toxicity, and is considered to have low potency. The action of ethambutol on the mycoba