Synthesis of hydroxymethyl analogues of mannostatin A and their evaluation as inhibitors of GH38 α-mannosidases

Analogues of mannostatin A were synthesised and evaluated as inhibitors of GH38 α-mannosidases. Different regioselectivity of aziridine opening with sodium methanethiolate was observed and investigated by quantum mechanics calculations.

[1]  J. Kóňa,et al.  Synthesis of N-benzyl substituted 1,4-imino-l-lyxitols with a basic functional group as selective inhibitors of Golgi α-mannosidase IIb. , 2019, Bioorganic chemistry.

[2]  J. Moncol’,et al.  Synthesis of 4a-Carba-d-lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α-Mannosidases , 2019, European Journal of Organic Chemistry.

[3]  J. Moncol’,et al.  Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases , 2018, Beilstein journal of organic chemistry.

[4]  A. F. Zahoor,et al.  Nucleophilic ring opening reactions of aziridines , 2018, Molecular Diversity.

[5]  I. Wilson,et al.  N‐Benzyl Substitution of Polyhydroxypyrrolidines: The Way to Selective Inhibitors of Golgi α‐Mannosidase II , 2018, ChemMedChem.

[6]  V. Sládek,et al.  In silico analysis of interaction pattern switching in ligandreceptor binding in Golgi α-mannosidase II induced by the protonated states of inhibitors. , 2017, Physical chemistry chemical physics : PCCP.

[7]  D. Rendić,et al.  Characterisation of class I and II α-mannosidases from Drosophila melanogaster , 2013, Glycoconjugate Journal.

[8]  U. Rinner,et al.  Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI2-Mediated Reformatsky Reaction , 2013, European journal of organic chemistry.

[9]  D. Rose,et al.  Structure, mechanism and inhibition of Golgi α-mannosidase II. , 2012, Current opinion in structural biology.

[10]  Jinhong Chang,et al.  Design, synthesis, and biological evaluation of N-alkylated deoxynojirimycin (DNJ) derivatives for the treatment of dengue virus infection. , 2012, Journal of medicinal chemistry.

[11]  S. Stankovic,et al.  Regioselectivity in the ring opening of non-activated aziridines. , 2012, Chemical Society reviews.

[12]  D. H. Williams,et al.  Iminosugars past, present and future: medicines for tomorrow. , 2011, Drug discovery today.

[13]  G. Boons,et al.  The Molecular Basis of Inhibition of Golgi α‐Mannosidase II by Mannostatin A , 2009, Chembiochem : a European journal of chemical biology.

[14]  Robert J Woods,et al.  Structural basis of the inhibition of Golgi alpha-mannosidase II by mannostatin A and the role of the thiomethyl moiety in ligand-protein interactions. , 2006, Journal of the American Chemical Society.

[15]  C. K. Chu,et al.  Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS. , 2006, Journal of medicinal chemistry.

[16]  T. Morikawa,et al.  Chemical Modification of the α‐Mannosidase Inhibitor Mannostain A: Synthesis of a Potent Inhibitor 1L‐(1,2,3,5/4)‐5‐Amino‐4‐O‐methyl‐1,2,3,4‐cyclopentanetetrol , 2005 .

[17]  I. Lundt,et al.  Synthesis of aminocyclopentanols: α-D-galacto configured sugar mimics , 2005 .

[18]  A. Vasella,et al.  Synthesis and Oxidation of N‐Aminoglyconolactams: A Synthesis of Mannostatin A , 2004 .

[19]  J. Reymond,et al.  Structure-activity relationships in aminocyclopentitol glycosidase inhibitors. , 2004, Organic & biomolecular chemistry.

[20]  X. Eric Hu,et al.  Nucleophilic ring opening of aziridines , 2004 .

[21]  Sean McSweeney,et al.  The Structure of Bovine Lysosomal α-Mannosidase Suggests a Novel Mechanism for Low-pH Activation , 2003 .

[22]  T. Iwama,et al.  An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-que , 2002, Journal of the American Chemical Society.

[23]  Mikael Bols,et al.  Recent developments of transition-state analogue glycosidase inhibitors of non-natural product origin. , 2002, Chemical reviews.

[24]  D. Kuntz,et al.  Structure of Golgi α‐mannosidase II: a target for inhibition of growth and metastasis of cancer cells , 2001, The EMBO journal.

[25]  P. Vogel,et al.  Amino(hydroxymethyl)cyclopentanetriols, an Emerging Class of Potent Glycosidase Inhibitors—Part I: Synthesis and Evaluation of β‐D‐Pyranoside Analogues in the manno, gluco, galacto, and GlcNAc Series , 2001, Chembiochem : a European journal of chemical biology.

[26]  J. Treadway,et al.  Glycogen phosphorylase inhibitors for treatment of type 2 diabetes mellitus , 2001, Expert opinion on investigational drugs.

[27]  T. Morikawa,et al.  Synthesis of a potent aminocyclitol alpha-mannosidase inhibitor, 1L-(1,2,3,5/4)-5-amino-4-O-methyl-1,2,3,4-cyclopentanetetrol. , 2000, Bioorganic & medicinal chemistry letters.

[28]  J. Reymond,et al.  Synthesis and Evaluation of Aminocyclopentitol Inhibitors of β-Glucosidases , 2000 .

[29]  N Zitzmann,et al.  Imino sugars inhibit the formation and secretion of bovine viral diarrhea virus, a pestivirus model of hepatitis C virus: implications for the development of broad spectrum anti-hepatitis virus agents. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[30]  T. Morikawa,et al.  Synthesis and biological evaluation of alpha-mannosidase inhibitory activity of three deoxy derivatives of mannostatin A. , 1999, Bioorganic & medicinal chemistry letters.

[31]  A. Siriwardena,et al.  Synthesis and Biological Activity of Natural Aminocyclopentitol Glycosidase Inhibitors: Mannostatins, Trehazolin, Allosamidins, and Their Analogues. , 1999, Chemical reviews.

[32]  S. Ogawa,et al.  SYNTHESIS AND GLYCOSIDASE INHIBITORY ACTIVITY OF FIVE STEREOISOMERS OF 5-AMINO-5-C-METHYL-1,2,3,4-CYCLOPENTANETETROL , 1998 .

[33]  P. Mariano,et al.  A Demonstration of the Synthetic Potential of Pyridinium Salt Photochemistry by Its Application to a Stereocontrolled Synthesis of (+)-Mannostatin A(1). , 1998, The Journal of organic chemistry.

[34]  C. K. Chu,et al.  Synthesis of L-ribofuranosyl C-nucleosides. , 1997, Carbohydrate research.

[35]  H. Kimura,et al.  Synthesis and biological evaluation of potent glycosidase inhibitors: N-phenyl cyclic isourea derivatives of 5-amino- and 5-amino-C-(hydroxymethyl)-1,2,3,4-cyclopentanetetraols. , 1997, Bioorganic & medicinal chemistry.

[36]  K. Moremen,et al.  Cloning, Expression, Purification, and Characterization of the Human Broad Specificity Lysosomal Acid α-Mannosidase* , 1996, The Journal of Biological Chemistry.

[37]  J. Dennis,et al.  Inhibitors of carbohydrate processing: A new class of anticancer agents. , 1995, Clinical Cancer Research.

[38]  P. Fuchs,et al.  Methanesulfenyl triflate promoted iminosulfenylation of an allylic trichloroacetimidate. An efficient and stereospecific total synthesis of (+) mannostatin A , 1994 .

[39]  B. Ganem,et al.  Synthetic Studies on Mannostatin A and Its Derivatives: A New Family of Glycoprotein Processing Inhibitors , 1994 .

[40]  B. Trost.  Abiological catalysis for synthetic efficiency , 1992 .

[41]  C. Unger,et al.  Deprotonation of 5,6‐Dihydro‐5‐methylene‐4H‐1,2‐oxazines and Regioselective Reactions with Electrophiles , 1991 .

[42]  I. Goldberg,et al.  Reactions of lithium salts of O‐alkyl oximes with halogens: A highly stereoselective oxidative coupling of 5,6‐dihydro‐3‐methyl‐4H‐1,2‐oxazine , 1991 .

[43]  N. Itoh,et al.  α-Cyano-α-fluorophenylacetic acid (CFPA) : a new reagent for determining enantiomeric excess that gives very large 19F NMR Δδ values , 1991 .

[44]  S. Knapp,et al.  SYNTHESIS OF THE MANNOSIDASE II INHIBITOR MANNOSTATIN A , 1991 .

[45]  S. Osborne,et al.  Enol Borinates in Organic Synthesis: Regioselective α-Sulphenylation and α-Selenenylation of Ketones , 1991 .

[46]  D. Winkler,et al.  Design of potential anti-HIV agents. 1. Mannosidase inhibitors. , 1989, Journal of medicinal chemistry.

[47]  T. Aoyagi,et al.  Mannostatins A and B: new inhibitors of alpha-D-mannosidase, produced by Streptoverticillium verticillus var. quintum ME3-AG3: taxonomy, production, isolation, physico-chemical properties and biological activities. , 1989, The Journal of antibiotics.

[48]  I. Hillebrand,et al.  Microbial α-Glucosidase Inhibitors: Chemistry, Biochemistry, and Therapeutic Potential , 1988 .

[49]  P. Novikoff,et al.  Effects of swainsonine on rat liver and kidney: biochemical and morphological studies , 1985, The Journal of cell biology.

[50]  D. Tulsiani,et al.  Swainsonine inhibits the biosynthesis of complex glycoproteins by inhibition of Golgi mannosidase II. , 1982, The Journal of biological chemistry.

[51]  B. Trost.  .alpha.-Sulfenylated carbonyl compounds in organic synthesis , 1978 .

[52]  Andor Furst,et al.  Über Steroide und Sexualhormone. 160. Mitteilung. 2α, 3α‐ und 2β, 3β‐Oxido‐chlolestane; Konfiguration der 2‐Oxy‐cholestane , 1949 .