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1.
J Am Chem Soc ; 145(16): 9003-9010, 2023 04 26.
Artigo em Inglês | MEDLINE | ID: mdl-37040604

RESUMO

The infection of Campylobacter jejuni results in a significant diarrhea disease, which is highly fatal to young children in unindustrialized countries. Developing a new therapy is required due to increasing antibiotic resistance. Herein, we described a total synthesis of a C. jejuni NCTC11168 capsular polysaccharide repeating unit containing a linker moiety via an intramolecular anomeric protection (iMAP) strategy. This one-step 1,6-protecting method structured the challenging furanosyl galactosamine configuration, facilitated further concise regioselective protection, and smoothed the heptose synthesis. The tetrasaccharide was constructed in a [2 + 1 + 1] manner. The synthesis of this complicated CPS tetrasaccharide was completed in merely 28 steps, including the preparation of all the building blocks, construction of the tetrasaccharide skeleton, and functional group transformations.


Assuntos
Campylobacter jejuni , Criança , Humanos , Pré-Escolar , Polissacarídeos , Heptoses , Oligossacarídeos , Cápsulas Bacterianas
2.
ACS Chem Neurosci ; 7(8): 1107-11, 2016 08 17.
Artigo em Inglês | MEDLINE | ID: mdl-27276519

RESUMO

Ganglioside Hp-s1 is isolated from the ovary of sea urchin Diadema setosum. It exhibited better neuritogenic activity than GM1 in pheochromocytoma 12 cells. To explore the roles of glucosyl moiety of Hp-s1 in contributing to the neurogenic activity, we developed feasible procedures for synthesis of Hp-s1 analogues (2a-2f). The glucosyl moiety of Hp-s1 was replaced with α-glucose, α-galactose, ß-galactose, α-mannose, and ß-mannose, and their biological activities on SH-SY5Y cells and natural killer T (NKT) cells were evaluated. We found that the orientation of C-2 hydroxyl group at glucosyl moiety of Hp-s1 plays an important role to induce neurite outgrowth of SH-SY5Y cells. Surprisingly, compound 2d could activate NKT cells to produce interleukin 2, although it did not show great activity on neurite outgrowth of SH-SY5Y cells. In general, the Hp-s1 might be considered as a lead compound for the development of novel drugs aimed at modulating the activity of neuronal cells.


Assuntos
Diferenciação Celular/efeitos dos fármacos , Gangliosídeo G(M1) , Neurogênese/efeitos dos fármacos , Animais , Configuração de Carboidratos , Linhagem Celular Tumoral , Citocinas/metabolismo , Gangliosídeo G(M1)/análogos & derivados , Gangliosídeo G(M1)/química , Gangliosídeo G(M1)/farmacologia , Glicosilação/efeitos dos fármacos , Humanos , Células Matadoras Naturais/efeitos dos fármacos , Células Matadoras Naturais/metabolismo , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Camundongos , Modelos Químicos , Estrutura Molecular , Neuritos/efeitos dos fármacos , Neuroblastoma
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