5627-25-8Relevant academic research and scientific papers
Biological upgrading of 3,6-anhydro-l-galactose from agarose to a new platform chemical
Kim, Dong Hyun,Liu, Jing-Jing,Lee, Jae Won,Pelton, Jeffrey G.,Yun, Eun Ju,Yu, Sora,Jin, Yong-Su,Kim, Kyoung Heon
, p. 1776 - 1785 (2020)
Recently, the utilization of renewable biomass instead of fossil fuels for producing fuels and chemicals has received much attention due to the global climate change. Among renewable biomass, marine algae are gaining importance as third generation biomass feedstocks owing to their advantages over lignocellulose. Particularly, red macroalgae have higher carbohydrate contents and simpler carbohydrate compositions than other marine algae. In red macroalgal carbohydrates, 3,6-anhydro-l-galactose (AHG) is the main sugar composing agarose along with d-galactose. However, AHG is not a common sugar and is chemically unstable. Thus, not only AHG but also red macroalgal biomass itself cannot be efficiently converted or utilized. Here, we biologically upgraded AHG to a new platform chemical, its sugar alcohol form, 3,6-anhydro-l-galactitol (AHGol), an anhydrohexitol. To accomplish this, we devised an integrated process encompassing a chemical hydrolysis process for producing agarobiose (AB) from agarose and a biological process for converting AB to AHGol using metabolically engineered Saccharomyces cerevisiae to efficiently produce AHGol from agarose with high titers and yields. AHGol was also converted to an intermediate chemical for plastics, isosorbide. To our knowledge, this is the first demonstration of upgrading a red macroalgal biomass component to a platform chemical via a new biological route, by using an engineered microorganism.
Synthesis of peracetylated C-1-deoxyalditol- and C-glycoside-dipyrranes via dithioacetal derivatives
Ló, Stephanie M.S.,Cunico, Juliana C.,Ducatti, Diogo R.B.,Orsato, Alexandre,Duarte, M. Eugênia R.,Barreira, Sandra M.W.,Noseda, Miguel D.,Gon?alves, Alan G.
supporting information, p. 1137 - 1140 (2013/05/08)
Dipyrranes bearing peracetylated mono- or disaccharidic C-1-deoxyalditol moieties were prepared from d-galactose, d-glucose, d-mannose, and lactose. A partially hydrolyzed polysaccharide (agarose) was also used as starting material for the synthesis of a disaccharide-containing C-glycoside dipyrrane. These compounds were synthesized as follows: the sugar starting materials were first submitted to a mercaptolysis-acetylation one-pot procedure (EtSH/HCl-Ac 2O/pyridine). The resulting peracetylated diethyl dithioacetals were converted into dipyrranes through carbonyl deprotection (H5IO 6, THF-Et2O) followed by TFA-catalyzed pyrrole condensation with yields up to 62%. Overall yields from sugar starting materials were up to 49%.
Matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry analysis of oligosaccharides and oligosaccharide alditols obtained by hydrolysis of agaroses and carrageenans, two important types of red seaweed polysaccharides
Fatema, M.Kaniz,Nonami, Hiroshi,Ducatti, Diogo R.B.,Goncalves, Alan G.,Duarte, M. Eugenia R.,Noseda, Miguel D.,Cerezo, Alberto S.,Erra-Balsells, Rosa,Matulewicz, Maria C.
experimental part, p. 275 - 283 (2010/04/02)
MALDI-TOF mass spectrometry analyses of several oligosaccharides (aldoses) and oligosaccharide alditols derived from agaroses, kappa- and iota-carrageenans using different matrices (2,5-dihydroxybenzoic acid, nor-harmane, ferulic acid, and the ionic liqui
