Stereospecific obtention of building blocks for - hydroxycarboxylic acids: D- and L-arabinose approach

Stereospecific obtention of building blocks for - hydroxycarboxylic acids: D- and L-arabinose approach

Soares, Fábio da Paixão; Doboszewski, Bogdan

Abstract:

The Lipids A, constituents of the lipopolysaccharides from the outer membrane of Gram-negative bacteria are highly toxic and potentially lethal via overactivation of the immune system. However, in the case of cancer or AIDS patients, immune activation can be beneficial. One can therefore consider analogs of the Lipids A as potential immunity boosters without their toxic character. Since -hydroxycarboxilic acids are one of the components of Lipids A, their general synthesis in chiral forms for further work is desired. Reported here is a stereospecific synthesis of the chiral building blocks 1 and 2 which permit obtention of the -hydroxycarboxylic acids of variable moiety R.

The Lipids A, constituents of the lipopolysaccharides from the outer membrane of Gram-negative bacteria are highly toxic and potentially lethal via overactivation of the immune system. However, in the case of cancer or AIDS patients, immune activation can be beneficial. One can therefore consider analogs of the Lipids A as potential immunity boosters without their toxic character. Since -hydroxycarboxilic acids are one of the components of Lipids A, their general synthesis in chiral forms for further work is desired. Reported here is a stereospecific synthesis of the chiral building blocks 1 and 2 which permit obtention of the -hydroxycarboxylic acids of variable moiety R.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0022-1

Referências bibliográficas

• [1] 1 Carbohydrate-based drug discovery. Wong, C.-H., ed. Wiley-VCH, 2003.
• [2] 2 Carbohydrates in chemistry and biology. Ernst, B.; Hart, G.W.; Sinaÿ, P., eds. Wiley-VCH, 2000.

Como citar:

Soares, Fábio da Paixão; Doboszewski, Bogdan; "Stereospecific obtention of building blocks for - hydroxycarboxylic acids: D- and L-arabinose approach", p-22-22. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0022-1