- Synthesis of 4a-Carba-d-lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α-Mannosidases
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A synthetic approach to 4a-carba-d-lyxofuranose derivatives starting from d-lyxose is described. The protected 4a-carba-β-d-lyxofuranose was employed as the key intermediate for the synthesis of 4a-carba-d-lyxofuranose derivatives including novel 1-amino-1-deoxy-4a-carba-d-lyxofuranoses. Synthesized 4a-carba-d-lyxofuranoses were evaluated as inhibitors of GH38 α-mannosidases, namely, the Golgi (GMIIb) and lysosomal (LManII) α-mannosidases from Drosophila melanogaster and commercial Jack bean α-mannosidase (JBMan) from Canavalia ensiformis. The biochemical evaluation revealed that only 1-amino-1-deoxy-4a-carba-β-d-lyxofuranose exhibited reasonable inhibitory activity against GMIIb (IC50 = 200 μm). In addition, the results of biological evaluation were discussed by means of molecular modelling.
- Zaji?ková, Mária,Monco?, Ján,?esták, Sergej,Kóňa, Juraj,Koó?, Miroslav,Bella, Maro?
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p. 1114 - 1124
(2019/01/24)
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- Biocatalytical Transformations- VI. The 4-Acetamido-cyclopent-2-ene Carboxylate Route Revisited: Synthesis of (+)- and (-)-Aristeromycin
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Enantiomerically pure (+)-as well as (-)-aristeromycin can be synthesized starting from (+)- or (-)-butyl (or hexyl) 4-acetamido-cyclopent-2-ene carboxylate; these carboxylates are easily obtained from their corresponding racemates by hydrolysis with the lipase from Candida rugosa.
- Csuk, Rene,Doerr, Petra
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p. 5789 - 5798
(2007/10/02)
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- Synthesis of carbocyclic nucleosides from 2-azabicyclo[2.2.1]hept-5-en-3-ones: Sodium borohydride-mediated carbon-nitrogen bond cleavage of five- and six-membered lactams
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Various carbocyclic ribofuranosyl nucleosides were stereoselectively synthesized through a small number of steps from 2-azabicyclo[2.2.1]hept-5-en-3-ones by the use of sodium borohydride-mediated C-N bond cleavage as a key step. Ready availability of a no
- Katagiri,Muto,Nomura,Higashikawa,Kaneko
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p. 1112 - 1122
(2007/10/02)
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- Synthesis of cyclopentane analogs of (2'- and 3'-deoxy-erythro-pentofuranosyl and ribofuranosyl)-2-thiouracil nucleosides
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Three new carbocyclic analogus of nucleosides having the 2-thiouracil base have been synthesized.The cyclopentyl groups in these nucleosides are (+/-)- (see 31), (+/-)- (see 32) and (+/-)- (see 33).The nucleosides were prepared by coupling the appropriate hydroxy derivatives of cis-3-aminocyclopentanemethanol with 3-ethoxypropenoyl isothiocyanate (21) followed by cyclization in 15 N aqueous ammonia to give the 2-thiouracil nucleosides.In addition a modified and shortenedsynthetic route is described for the synthesys of (+/-)-(1β,2α,3α,4β)-4-amino-2,3-dihydroxy-cyclopentanemethanol (19).The (1)H nmr spectra at 200 MHz of all of the synthetic intermediates, the 2-thiouracil nucleosides, and of the corresponding carbocyclic analogs of uracil nucleosides are discussed.It is shown that each nucleoside has a characteristically unique (1)H nmr spectrum and that in general the protons in the sulfur-containing compounds resonate at lower filds than those in the corresponding oxygen-containing compounds.The magnitude of this downfield shift is inversely related to the number of bonds separating a particular proton from the sulfur atom.
- Hronowski, Lucjan J. J.,Szarek, Walter A.
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p. 1620 - 1629
(2007/10/02)
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- Cyclit-Reaktionen, II. Darstellung von Bausteinen zur Synthese carbocyclischer Furanose-Analoga
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The four isomeric hydroxycyclopentenmethanols 6a to 9a can easily be made by allylhydroxylation of the epoxides 2 and 4 with phenyl selenide.In a second way the pair 8a and 9a has been synthesized from 11 via 15.As the preparation of 20 demonstrates, the functionalisation of 6a to 9a to carbocyclic furanoses is possible.The dicarboxylic diethyl esters 23 and 33 can be converted into models for carbocyclic ketofuranoses.
- Paulsen, Hans,Maass, Uwe
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p. 346 - 358
(2007/10/02)
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