Rational design of aza sugars via biocatalysis: mannojirimycin and other glycosidase inhibitors (original) (raw)

Synthesis of 2-Azabicyclo[3.2.2]nonane-Derived Monosaccharide Mimics and Their Evaluation as Glycosidase Inhibitors

Stephan Buser

Helvetica Chimica Acta, 2006

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Microbial Oxidation of Aromatics in Enantiocontrolled Synthesis. 2. Rational Design of Aza Sugars (endo-Nitrogenous). Total Synthesis of (+)-Kifunensine, Mannojirimycin, and Other Glycosidase Inhibitors

Horacio Olivo

Journal of the American Chemical Society, 1994

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Glycosidase Inhibitors: Synthesis of Enantiomerically Pure Aza-Sugars from Schiff Base Amino Esters via Tandem Reduction-Alkenylation and Osmylation

Robin Polt

The Journal of Organic Chemistry, 1999

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From 1,4-Disaccharide to 1,3-Glycosyl Carbasugar: Synthesis of a Bespoke Inhibitor of Family GH99 Endo-α-mannosidase

Oscar Millet

Organic Letters, 2018

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Synthesis of regio- and stereospecifically C-deuterated derivatives of glycosidase inhibitors 1-deoxymannonojirimycin and 2,5-dideoxy-2,5-imino-d-mannitol by intramolecular reductive amination employing deuterium gas

Christian Mirtl

Carbohydrate Research, 1998

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New Synthetic Seven-Membered 1-Azasugars Displaying Potent Inhibition Towards Glycosidases and Glucosylceramide Transferase

Jérome Marrot

ChemBioChem, 2008

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Enantioselective and Protecting Group-Free Synthesis of 1-Deoxythionojirimycin, 1-Deoxythiomannojirimycin, and 1-Deoxythiotalonojirimycin

Srinivasan Chandrasekaran

The Journal of Organic Chemistry, 2010

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Enantioselective and Protecting Group-Free Synthesis of I-Deoxythionojirimycin, 1-Deoxythiomannojirimycin, and 1-Deoxythiotalonojirimycin

Srinivasan Chandrasekaran

Journal of Organic Chemistry, 2010

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Cyclic Amidine Sugars as Transition-State Analogue Inhibitors of Glycosidases: Potent Competitive Inhibitors of Mannosidases

B. Murray

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Synthesis and evaluation of a bicyclic deo×ymannojirimycin derivative as a potential glycosidase inhibitor

Kelly Tanaka

Canadian Journal of Chemistry-revue Canadienne De Chimie, 1998

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Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

Inge Lundt

Carbohydrate Research, 2000

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Towards a stable noeuromycin analog with a d-manno configuration: Synthesis and glycosidase inhibition of d-manno-like tri- and tetrahydroxylated azepanes

Yves Blériot

Bioorganic & Medicinal Chemistry, 2012

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Synthesis of Fused Oxa-Aza Spiro Sugars from D-Glucose-Derived δ-Lactone as Glycosidase Inhibitors

Yashwant Vankar

European Journal of Organic Chemistry, 2010

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7-Oxanorbornane and Norbornane Mimics of a Distortedβ-D-Mannopyranoside: Synthesis and Evaluation asβ-Mannosidase Inhibitors

Stephan Buser

Helvetica Chimica Acta, 2005

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Sugar-Derived Di- and Tetrahydropyridazinones: Synthesis of New Glycosidase Inhibitors

Andrea Vasella

Helvetica Chimica Acta, 2000

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Synthesis of 1,5-dideoxy-3-O-(α-D-mannopyranosyl)-1,5-imino-D-mannitol and 1,5-dideoxy-3-O-(α-D-glucopyranosyl)-1,5-imino-D-mannitol: Powerful inhibitors of endomannosidase

Raymond Dwek

Tetrahedron: Asymmetry, 1993

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Design and synthesis of mannose analogues as inhibitors of α-mannosidase

Basudeb Achari

Tetrahedron, 1994

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Inhibition of α-mannosidases by seven carbon sugars: Synthesis of some seven carbon analogues of mannofuranose

George Fleet

Tetrahedron, 1992

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Iminoheptitols as glycosidase inhibitors: Synthesis of α-homomannojirimycin, 6-epi-α-homomannojirimycin and of a highly substituted pipecolic acid

George Fleet

Tetrahedron, 1992

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Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from d-mannitol derived nitroolefins

Yashwant Vankar

Tetrahedron: Asymmetry, 2013

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Synthesis and evaluation as glycosidase inhibitors of 2,5-imino-d-glucitol and 1,5-imino-d-mannitol related derivatives

Matthias Böhm

Bioorganic & Medicinal Chemistry, 2000

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N-Heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid a novel scaffold for the design of uncompetitive α-glucosidase inhibitors

Stefano Biondi

Bioorganic & Medicinal Chemistry, 2013

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Intermediates for incorporation of tetrahydroxypipecolic acid analogues of α- and β-d-mannopyranose into combinatorial libraries: unexpected nanomolar-range hexosaminidase inhibitors. Synthesis of α- and β-homomannojirimycin

Ana Winters

Tetrahedron: Asymmetry, 1998

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Metabolic oligosaccharide engineering with N-Acyl functionalized ManNAc analogs: Cytotoxicity, metabolic flux, and glycan-display considerations

shivam shah

Biotechnology and Bioengineering, 2011

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Hybrid sugars as glycosidase inhibitors en route to 2-deoxy-2-amino C-glycosyl amino acids

Yashwant Vankar

Tetrahedron Letters, 2006

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Synthesis of the α-Mannosidase inhibitors swainsonine [(1S, 2R, 8R, 8aR)-1,2,8-trihydroxyoctahydroindolizine] and 1,4-dideoxy-1,4-imino-d-mannitol from mannose

Bharat Bashyal, George Fleet

Tetrahedron, 1987

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Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks

Teodora Bavaro

Molecules

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Synthesis of Pyrrolidine-Based Imino Sugars as Glycosidase Inhibitors

Yashwant Vankar

European Journal of Organic Chemistry, 2007

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Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity

Rama P Tripathi

Bioorganic & Medicinal Chemistry Letters, 2009

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Reductive Amination of Glycosyl Aldoses: Synthesis of N‐Glycosylated β‐Glycosyl Amino Alcohols and their Enzyme Inhibitory Effect

Rama P Tripathi

Cheminform, 2006

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Efficient access to azadisaccharide analogues

Christine Gravier-pelletier

Tetrahedron Letters, 2001

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Improved cellular inhibitors for glycoprotein processing α-glucosidases: biological characterisation of alkyl- and arylalkyl-N-substituted deoxynojirimycins

raymond dwek

Tetrahedron: Asymmetry, 2009

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Molecular Engineering of Fungal GH5 and GH26 Beta-(1,4)-Mannanases toward Improvement of Enzyme Activity

Jean-guy Berrin

PLoS ONE, 2013

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