ABSTRACT
The immunodominant epitope α-d-Galp-(1â¯ââ¯3)-ß-d-Galp-(1â¯ââ¯4)-d-GlcNAc, expressed in the mucins of the infective trypomastigote stage of Trypanosoma cruzi has been proposed for multiple clinical applications, from serodiagnosis of protozoan caused diseases to xenotransplantation or cancer vaccinology. It was previously shown that the analogue trisaccharide, with glucose in the reducing end instead of GlcNAc, was as efficient as the natural trisaccharide for recognition of chagasic antibodies. Here we describe the synthesis of α-d-Galp-(1â¯ââ¯3)-ß-d-Galp-(1â¯ââ¯4)-d-Glcp functionalized as the 6-aminohexyl glycoside and its conjugation to BSA using the squarate method. The conjugate of 6-aminohexyl α-d-Galp-(1â¯ââ¯3)-ß-d-Galp was also prepared. Both neoglycoconjugates were recognized by serum samples of Trypanosoma cruzi-infected individuals and thus, are promising tools for the improvement of Chagas disease diagnostic applications.
Subject(s)
Chagas Disease/drug therapy , Epitopes/immunology , Glycoconjugates/therapeutic use , Carbohydrate Conformation , Chagas Disease/immunology , Epitopes/chemistry , Glycoconjugates/chemical synthesis , Glycoconjugates/chemistry , HumansABSTRACT
The solid state structure of 1-((1H-benzotriazol-1-yl)methyl)naphthalen-2-ol, C17H13N3O, shows that this Mannich base crystallizes forming intermolecular N...HO hydrogen bonds, rather than intramolecular ones. Factors contributing to this choice of hydrogen-bonding mode are discussed. The compound crystallizes in the monoclinic system, P2(1)/c space group, with lattice constants: a = 11.7934(9) A, b = 14.3002(14) A, c = 8.4444(8) A, beta = 106.243(5) deg, V = 1367.3(2) A(3), Z = 4, F(000) = 576, R(1) = 6.96%, wR(2) = 11.4%.
Subject(s)
Naphthalenes/chemistry , Triazoles/chemistry , Crystallization , Crystallography, X-Ray , Hydrogen Bonding , Molecular StructureABSTRACT
In the title structure, C(18)H(20)N(4), the aromatic rings are almost orthogonal [81.6â (2)°]. The mol-ecule has symmetry 2 since it is situated on a crystallographic twofold axis. There are only weak inter-molecular inter-actions present in the structure, notably C-Hâ¯π-electron ring inter-actions. The (1)H and (13)C NMR spectra are in accordance with the X-ray structure analysis.
