Papers by Giorgio Catelani
Carbohydrate research, Jan 18, 2017
Carbohydrate mimics have been studied for a long time as useful sugar substitutes, both in the in... more Carbohydrate mimics have been studied for a long time as useful sugar substitutes, both in the investigation of biological events and in the treatment of sugar-related diseases. Here we report further evaluation of the capabilities of inositols as carbohydrate substitutes. The conformational features of an inositol-model of a simplified repeating unit corresponding to the capsular polysaccharide of Streptococcus pneumoniae 19F has been evaluated by computational analysis, and compared to the native repeating unit. The inositol mimic was synthesized, and its experimental spectroscopic data allowed for verification of the theoretical results.
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J Org Chem, 1981
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Http Dx Doi Org 10 1080 07328300802030845, Jun 12, 2008
The synthetic access of either β‐d‐ManNAc‐(1→4)‐d‐Glc (5) is β‐d‐TalNAc‐(1→4)‐d‐Glc (6) disacchar... more The synthetic access of either β‐d‐ManNAc‐(1→4)‐d‐Glc (5) is β‐d‐TalNAc‐(1→4)‐d‐Glc (6) disaccharides has been effectively improved with respect to previous syntheses (J. Carbohydr. Chem. 2000, 19, 79–91 and 2004, 23, 179–190), optimizing the preparation of suitably protected 4‐O‐(2‐acetamido‐2‐deoxy‐3,4‐O‐isopropylidene‐β‐d‐talopyranosyl)‐2,3∶5,6‐di‐O‐isopropylidene‐aldehydo‐d‐glucose dimethyl acetal derivatives obtained by complete stereoselective LiAlH4 reduction of new 2′‐oximino precursors derived from lactose. The affinity of the disaccharides 5 and
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J Carbohyd Chem, 1999
The title compound, previously unreported in either enantioform, and its 2,6-di-O-benzyl derivati... more The title compound, previously unreported in either enantioform, and its 2,6-di-O-benzyl derivative have been synthesized through a stereocontrolled epimerization at C-2 of 6-O-protected methyl 3,4-O-isopropylidene-5-C-methoxy-β-D-galactopyranosides. The epimerization, performed through a high yielding sequence of oxidation-reduction owing to the cooperative role of the equatorial C-1 aglycon and the steric hindrance of the isopropylidene group, turned out to be completely diastereoselective. Whereas
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Bioorganic Medicinal Chemistry Letters, Nov 18, 2002
The DBU-promoted intramolecular aldol condensation of two partially protected L-lyxo-hexos-5-ulos... more The DBU-promoted intramolecular aldol condensation of two partially protected L-lyxo-hexos-5-ulose derivatives (8 and 9), in turn obtained starting from methyl beta-D-galactopyranoside, takes place with fairly good yield and complete diastereoselectivity to give 2L-(2,3,6/4,5)-pentahydroxycyclohexanone derivatives, 10 and 11. The stereoselective reduction of inosose 10 with sodium triacetoxyborohydride leads, after catalytic debenzylation, to D-chiro-inositol (1), while the sodium borohydride reduction furnishes, with opposite stereoselectivity, a derivative of allo-inositol.
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Carbohydrate Research, Aug 17, 2009
The recently described [Attolino, E.; Bonaccorsi, F.; Catelani, G.; D&amp... more The recently described [Attolino, E.; Bonaccorsi, F.; Catelani, G.; D'Andrea, F. Carbohydr. Res. 2008, 343, 2545-2556.] beta-D-MaNAcp-(1-->4)-beta-D-Glcp thiophenyl glycosyl donor 3 was used in alpha-glycosylation reactions of OH-2 and OH-3 of the suitably protected p-MeO-benzyl alpha-l-rhamnopyranoside acceptors 7 and 8. Glycosylation of the axial OH-2 of 7 took place in high yield (76%) and with acceptable stereoselectivity (alpha/beta=3.4) leading to the protected trisaccharide alpha-11, corresponding to the repeating unit of Streptococcus pneumoniae 19F. The same reaction on equatorial OH-3 of acceptor 8 gave the trisaccharide alpha-15, a constituent of the repeating unit of S. pneumoniae 19A, but in lower yield (41%) and without stereoselection (alpha/beta=1:1.3). Utilizing the introduced orthogonal protection of OH-1 and OH-4'', the trisaccharide alpha-11 was transformed into a trisaccharide building block suitable for the synthesis of its phosphorylated oligomers.
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Cheminform, 2010
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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Eur J Org Chem, 2007
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Tetrahedron, Mar 3, 1997
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Tetrahedron, 1997
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Environmetal Science and Pollution Research International, Feb 1, 2003
A totally protected di-O-benzyl derivative of triacetonlactose dimethyl acetal was transformed in... more A totally protected di-O-benzyl derivative of triacetonlactose dimethyl acetal was transformed into a 4'-hexeno disaccharide by elimination of acetone with t-BuOK in DMF and subsequently in 5'-C-methoxy derivative by oxidation with MCPBA in methanol as a solvent. The hydrolysis of this latter compound affords 2,6-di-O-benzyl-L-arabino-aldohexosos-5-ulose, which by intramolecular aldol condensation with DBU gives an inosose that was stereoselectively reduced to epi-inositol. Therefore our synthetic strategy offers a new and simple method to transform lactose into carbocyclic monosaccharide analogues.
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Tetrahedron, 1989
Racemic isobutyl 3,4-anhydro-2,6-dideoxy-α--hexopyranoside, 3, was prepared starting from the cyc... more Racemic isobutyl 3,4-anhydro-2,6-dideoxy-α--hexopyranoside, 3, was prepared starting from the cycloadduct between 3-buten-2-one and isobutyl vinyl ether, through a sequence involving hydroboration-oxidation, mesylation, anomeric equilibration, elimination and epoxidation. ...
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Cheminform, 2003
ABSTRACT
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Carbohydrate Research, Jun 5, 2002
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Bioorg Medicinal Chem Letter, 2002
... Professor Serena Catalano. Giorgio Catelani Corresponding Author Contact Information , E-mail... more ... Professor Serena Catalano. Giorgio Catelani Corresponding Author Contact Information , E-mail The Corresponding Author , a , Antonino Corsaro b , Felicia D'Andrea a ,Manuela Mariani a and Venerando Pistarà b. a Dipartimento ...
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Bioresources, 2007
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Http Dx Doi Org 10 1080 07328309808001891, Aug 16, 2006
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J Carbohyd Chem, 2000
The 6-O-trityl derivative of 2,3:5,6:3′,4′-O-isopropylidenelactose dimethyl acetal (1) was conver... more The 6-O-trityl derivative of 2,3:5,6:3′,4′-O-isopropylidenelactose dimethyl acetal (1) was converted through an oxidation/oximation/reduction sequence involving the free 2-OH group of the D-galactose moiety into the protected disaccharide 5 in up to 75% yield. The complete deprotection of 5 produced the disaccharide 4-O-(2-acetamido-2-deoxy-β-D-talopyranosyl)-D-glucose (7a). The oxime LiAlH4 reduction step produced some unexpected side-products, the most abundant of which, the dimethyl acetal
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Papers by Giorgio Catelani