Chemistry:Arabitol

From HandWiki

Arabitol, or arabinitol, is a sugar alcohol. It can be formed by the reduction of either arabinose. Some organic acid tests check for the presence of D-arabitol, which may indicate overgrowth of intestinal microbes such as Candida albicans or other yeast/fungus species.[1]

Arabitol and lyxitol are diastereomeric pentitols, differing in the configuration of two stereocenters. Arabitol was initially produced, soon after its discovery, through the catalytic reduction of D-arabinose or D-lixose[2]. It can be obtained in two spatial forms: L-arabitol and D-arabitol.

Production

Industrial production of arabitol has traditionally relied on chemical reduction of oxidized arabinose derivatives, including lactones, arabinonic acid and lixonic acid. These processes require high temperatures (around 100 °C) and expensive catalysts, and generally involve extensive purification of the feedstock prior to catalytic reduction.[3]

Biotechnological production routes have also been developed.[4] L-arabitol can be obtained by microbial fermentation using organisms capable of metabolizing L-arabinose, including Candida tropicalis, Pichia stipitis and Debaryomyces hansenii, as well as genetically engineered strains of Saccharomyces cerevisiae. Most reported studies have used batch cultivation with synthetic L-arabinose as substrate, although lignocellulosic hydrolysates such as sisal bagasse and soybean flour hydrolysates have also been evaluated.[5][6]

References

  1. "Candida and Yeast Overgrowth". http://www.greatplainslaboratory.com/home/eng/candida.asp. 
  2. Hajny, G. J. (January 1964). "D-Arabitol Production by Endomycopsis chodati". Applied Microbiology 12 (1): 87–92. doi:10.1128/am.12.1.87-92.1964. ISSN 0003-6919. PMID 14111539. PMC 1058070. https://doi.org/10.1128/am.12.1.87-92.1964. 
  3. Kumdam, Himabindu; Narayana Murthy, Shweta; Gummadi, Sathyanarayana N (2013-05-09). "Production of ethanol and arabitol by Debaryomyces nepalensis: influence of process parameters". AMB Express 3 (1). doi:10.1186/2191-0855-3-23. ISSN 2191-0855. PMID 23659479. 
  4. Kordowska-Wiater, M. (2015-04-08). "Production of arabitol by yeasts: current status and future prospects". Journal of Applied Microbiology 119 (2): 303–314. doi:10.1111/jam.12807. ISSN 1364-5072. PMID 25809659. https://doi.org/10.1111/jam.12807. 
  5. de Medeiros, Lorena Lucena; da Silva, Flávio Luiz Honorato; de Queiroz, Angela Lima Menêses; de Oliveira, Ysrael Simões Lins; de Souza Junior, Evanildo Francisco; Madruga, Marta Suely; da Conceição, Marta Maria (2020-07-28). "Structural-chemical characterization and potential of sisal bagasse for the production of polyols of industrial interest". Brazilian Journal of Chemical Engineering 37 (3): 451–461. doi:10.1007/s43153-020-00049-3. ISSN 0104-6632. https://doi.org/10.1007/s43153-020-00049-3. 
  6. Garcia Sanchez, Rosa; Karhumaa, Kaisa; Fonseca, César; Sànchez Nogué, Violeta; Almeida, João RM; Larsson, Christer U; Bengtsson, Oskar; Bettiga, Maurizio et al. (2010-06-15). "Improved xylose and arabinose utilization by an industrial recombinant Saccharomyces cerevisiae strain using evolutionary engineering". Biotechnology for Biofuels 3 (1). doi:10.1186/1754-6834-3-13. ISSN 1754-6834. PMID 20550651. Bibcode2010BB......3...13G. 

Further reading