14904-83-7Relevant academic research and scientific papers
Stereoselective synthesis of 1-deoxynojirimycin, D-glucono-δ-lactam and D-altrono-δ-lactam from a common chiral intermediate derived from D-mannitol
Ravinder, Mettu,Reddy, Thatikonda Narendar,Mahendar, Budde,Rao, Vaidya Jayathirtha
, p. 287 - 302 (2013/02/26)
A stereoselective synthesis of 1-deoxynojirimycin, D-glucono-δ-lactam and D-altrono-δ-lactam were accomplished from a common chiral intermediate derived from D-mannitol. The key transformations in the synthesis include Miyashita C-2 selective endo-mode azide opening of epoxy alcohol and Sharpless asymmetric dihydroxylation. ARKAT-USA, Inc.
COMPOSITIONS COMPRISING NB-DNJ, NE-DNJ OR D-GLUCARO-DELTA-LACTAM AND THEIR USES FOR THE TREATMENT OF PAIN AND OTHER NEUROLOGICAL CONDITIONS
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Page/Page column 47-48, (2008/06/13)
Methods and compositions for the treatment of conditions including stress-associated, chronic pain, and neurodegenerative conditions in a mammal using a composition comprising NB-DNJ or a compound structurally similar thereto.
All eight stereoisomeric D-glyconic-δ-lactams: Synthesis, conformational analysis, and evaluation as glycosidase inhibitors
Nishimura, Yoshio,Adachi, Hayamitsu,Satoh, Takahiko,Shitara, Eiki,Nakamura, Hikaru,Kojima, Fukiko,Takeuchi, Tomio
, p. 4871 - 4882 (2007/10/03)
An efficient and general synthetic route to all eight stereoisomeric D-glycono-δ-lactams has been developed. The strategy involves, as a key step, a stereodivergent δ-lactam formation with configurational retention or inversion at C-4 of a starting γ-lactone to lead to two epimers of δ-lactam from one parent γ-lactone. Conformations of eight glycono-δ-lactams were examined by X-ray crystallographic analysis and molecular modeling. Analyses of conformation and glycosidase-inhibition provide useful information for the design of new glycosidase inhibitors.
A general approach to the synthesis of dideoxy and trideoxyiminoalditols from β-D-glycosides
Pistia, Gabriela,Hollingsworth, Rawle I.
, p. 467 - 472 (2007/10/03)
Imino sugars (also called azasugars), a class of compounds of which the 1,5-dideoxy and 1,5,6-trideoxyiminoalditols are members, are important glycosidase inhibitors with very high potential as drugs. Their potential therapeutic applications range from the treatment of diabetes to cancer and AIDS. We present here a general method for the preparation of such compounds with the D-gluco and D-galacto configurations starting from β-D-glycosides. The procedure is especially appealing because of its high stereoselectivity and straightforwardness. The key steps are the selective oxidation of the glycosides to hexulosonic acids and reduction of the oxime derivatives to lactams, which are further reduced to the target compounds. The C-6 position can be deoxygenated during the reduction if it bears an acetoxy group. Trideoxy imino sugars are then produced. Deacetylation prior to oxime reduction gives dideoxy compounds. (C) 2000 Elsevier Science Ltd.
A Facile Transformation of Sugar Lactones to Azasugars
Overkleeft, Herman S.,Wiltenburg, Jim van,Pandit, Upendra K.
, p. 4215 - 4224 (2007/10/02)
The synthesis of pyrano- and furano- sugar lactams from the corresponding lactones, in a five step sequence, is described.
An expedient stereoselective synthesis of gluconolactam
Overkleeft, Herman S.,Van Wiltenburg, Jim,Upendra Pandit
, p. 2527 - 2528 (2007/10/02)
An efficient synthesis of the title compound, starting from glucose, is described.
Amidine, amidrazone, and amidoxime derivatives of monosaccharide aldonolactams: Synthesis and evaluation as glycosidase inhibitors
Papandreou,Tong,Ganem
, p. 11682 - 11690 (2007/10/02)
The synthesis of amidine, amidrazone, and amidoxime derivatives of D-glucono, D-mannono, and D-galactonolactams, which are potent glycosidase inhibitors, is described. With their sugar-like structures and resonance-stabilized, partially positively charged anomeric carbons, these monosaccharide analogs mimic key conformational and electrostatic features of the corresponding glycopyranosyl cations. In the D-gluco series, all three derivatives are potent inhibitors of sweet almond β-glucosidase. Levels of inhibition remain nearly constant despite a 105 change in basicity, indicating that conformational flattening of the hydrolysis intermediate is more important for transition-state binding by the enzyme than charge development. The same D-gluco derivatives also interact with mannose- and galactose-processing enzymes. Considerably weaker inhibition is observed with 1β-amino-1-deoxynojirimycin, which embodies similar endocyclic and exocyclic nitrogens in an undistorted chair conformation. In the D-manno series, the amidrazone and amidoxime are potent inhibitors of jackbean α-mannosidase, mung bean α-mannosidase, fungal β-mannosidase, Golgi α-mannosidase I, α-mannosidase II, and soluble (or endoplasmic reticulum) α-mannosidase. The mannoamidrazone also inhibits Golgi α-mannosidase I and the endoplasmic reticulum mannosidase in vivo. In the D-galacto series, significant inhibition of almond β-glucosidase, bovine liver β-galactosidase, and green coffee bean α-galactosidase is observed, but little or no inhibition of amyloglucosidase.
Enzyme-catalyzed aldol condensation for asymmetric synthesis of azasugars: Synthesis, evaluation, and modeling of glycosidase inhibitors
Kajimoto, Tetsuya,Liu, Kevin K.-C.,Pederson, Richard L.,Zhong, Ziyang,Ichikawa, Yoshitaka,Porco Jr., John A.,Wong, Chi-Huey
, p. 6187 - 6196 (2007/10/02)
A combined fructose 1,6-diphosphate aldolase reaction and catalytic reductive amination has been used in the asymmetric synthesis of azasugars structurally corresponding to N-acetylglucosamine, N-acetylmannosamine, and deoxyhexoses. The 6-deoxyazasugars w
SYNTHESIS OF DEOXYNOJIRIMYCIN AND OF NOJIRIMYCIN δ-LACTAM
Fleet, George W.J.,Carpenter, Neil M.,Petursson, Sigthor,Ramsden, Nigel G.
, p. 409 - 412 (2007/10/02)
The syntheses of nojirimycin δ-lactam and of deoxynojirimycin from a divergent ido-furanose intermediate are reported.
