Search results for: Vanessa L. Campo

Items from 1 to 7 out of 7 results

article

Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion

Vanessa L. Campo, Irina M. Ivanova, Ivone Carvalho, Carla D. Lopes, more

Tetrahedron > 2015 > 71 > 39 > 7344-7353

Reaction of 2-(2-(2-azidoethoxy)ethoxy)ethyl 6-O-(prop-2-ynyl)-β-d-galactopyranoside (7) under CuAAC conditions gives rise to mixed cyclic and linear triazole-linked oligomers, with individual compounds up to d.p. 5 isolable, along with mixed larger oligomers. The linear compounds resolve en bloc from the cyclic materials by RP HPLC, but are separable by gel permeation chromatography. The triazole-linked...

article

α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi

Maristela B. Martins-Teixeira, Vanessa L. Campo, Monica Biondo, Renata Sesti-Costa, more

Bioorganic & Medicinal Chemistry > 2013 > 21 > 7 > 1978-1987

This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(αGalNAc)Ser] 3 and cyclo[Asp-(αGalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids αGalNAc-Ser 7 or αGalNAc-Thr 8 and the amino acid...

article

Design, synthesis and the effect of 1,2,3-triazole sialylmimetic neoglycoconjugates on Trypanosoma cruzi and its cell surface trans-sialidase

Vanessa L. Campo, Renata Sesti-Costa, Zumira A. Carneiro, João S. Silva, more

Bioorganic & Medicinal Chemistry > 2012 > 20 > 1 > 145-156

This work describes the synthesis of a series of sialylmimetic neoglycoconjugates represented by 1,4-disubstituted 1,2,3-triazole-sialic acid derivatives containing galactose modified at either C-1 or C-6 positions, glucose or gulose at C-3 position, and by the amino acid derivative 1,2,3-triazole fused threonine-3-O-galactose as potential TcTS inhibitors and anti-trypanosomal agents. This series...

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Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

Eva Galante, Corrada Geraci, Sebastiano Sciuto, Vanessa L. Campo, more

Tetrahedron > 2011 > 67 > 33 > 5902-5912

A new series of water-soluble tetravalent glycoclusters incorporating β-lactosyl residues attached to a central calix[4]arene core was synthesised using azide–alkyne Cu(I)-catalysed cycloaddition (‘click chemistry’). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14–21 atom spacer arms. The glycoclusters with a C ₄ ...

article

Application of copper(I)-catalysed azide/alkyne cycloaddition (CuAAC) ‘click chemistry’ in carbohydrate drug and neoglycopolymer synthesis

Valquiria Aragão-Leoneti, Vanessa L. Campo, Adriane S. Gomes, Robert A. Field, more

Tetrahedron > 2010 > 66 > 49 > 9475-9492

An overview of the potential application of copper(I)-catalysed azide/alkyne cycloaddition (CuAAC) ‘click chemistry’ in the synthesis of bioactive carbohydrates and neoglycopolymers is described.

article

‘Click chemistry’ synthesis of a library of 1,2,3-triazole-substituted galactose derivatives and their evaluation against Trypanosoma cruzi and its cell surface trans-sialidase

Ivone Carvalho, Peterson Andrade, Vanessa L. Campo, Paulo M.M. Guedes, more

Bioorganic & Medicinal Chemistry > 2010 > 18 > 7 > 2412-2427

Trypanosoma cruzi trans-sialidase (TcTS) plays a key role in the recognition and invasion of host cells and in enabling the parasite to escape the human immune response. To explore this potential drug target, we have synthesized a small library of substrate analogues based on 1,4-disubstituted 1,2,3-triazole derivatives of galactose modified at either the C-1 or C-6 positions. This was achieved by...

article

Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

Vanessa L. Campo, Maristela B. Martins, Carlos H.T.P. da Silva, Ivone Carvalho

Tetrahedron > 2009 > 65 > 27 > 5343-5349

This work describes the synthesis in solution of a series of related diketopiperazines with potential biological activities: cyclo(l-Pro-l-Ser), cyclo(l-Phe-l-Ser), cyclo(d-Phe-l-Ser) and the corresponding glycosylated analogs of the latter, cyclo[d-Phe-l-Ser(αGlcNAc)] and cyclo[d-Phe-l-Ser(βGlcNAc)]. The synthetic approach involved coupling reactions of –OH or O-glycosylated serine benzyl esters...

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Keywords

TRYPANOSOMA CRUZI (5)
CLICK CHEMISTRY (3)
TRANS-SIALIDASE (3)
TRIAZOLE (2)
CALIXSUGAR (1)
CALIX[4]ARENE (1)
CARBOHYDRATE BIOACTIVE COMPOUNDS (1)
COPPER(I)-CATALYSED AZIDE/ALKYNE CYCLOADDITION (1)
DIKETOPIPERAZINE (1)
DIPEPTIDE CYCLIZATION (1)
GALACTOSE (1)
GLYCOCLUSTER (1)
GLYCOSYL DIKETOPIPERAZINE (1)
GLYCOSYLATED AMINO ACID (1)
GLYCOSYLATION (1)
HUISGEN 1,3-DIPOLAR CYCLOADDITION (1)
MACROPHAGE INVASION (1)
MUCIN (1)
MULTIVALENCY (1)
NEOGLYCOPOLYMERS (1)
PSEUDO-GLYCOMACROCYCLES (1)
SIALYLMIMETICS (1)
SOLUTION-PHASE SYNTHESIS (1)
TRIAZOLE-LINKED OLIGOMERS (1)
‘CLICK CHEMISTRY’ (1)
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Journal

Tetrahedron (4)
Bioorganic & Medicinal Chemistry (3)

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Search results for: Vanessa L. Campo

Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion

α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi

Design, synthesis and the effect of 1,2,3-triazole sialylmimetic neoglycoconjugates on Trypanosoma cruzi and its cell surface trans-sialidase

Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

Application of copper(I)-catalysed azide/alkyne cycloaddition (CuAAC) ‘click chemistry’ in carbohydrate drug and neoglycopolymer synthesis

‘Click chemistry’ synthesis of a library of 1,2,3-triazole-substituted galactose derivatives and their evaluation against Trypanosoma cruzi and its cell surface trans-sialidase

Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

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