87936-86-5Relevant academic research and scientific papers
Asymmetric assembly of aldose carbohydrates from formaldehyde and glycolaldehyde by tandem biocatalytic aldol reactions
Szekrenyi, Anna,Garrabou, Xavier,Parella, Teodor,Joglar, Jess,Bujons, Jordi,Claps, Pere
, p. 724 - 729 (2015)
The preparation of multifunctional chiral molecules can be greatly simplified by adopting a route via the sequential catalytic assembly of achiral building blocks. The catalytic aldol assembly of prebiotic compounds into stereodefined pentoses and hexoses is an as yet unmet challenge. Such a process would be of remarkable synthetic utility and highly significant with regard to the origin of life. Pursuing an expedient enzymatic approach, here we use engineered D-fructose-6-phosphate aldolase from Escherichia coli to prepare a series of three- to six-carbon aldoses by sequential one-pot additions of glycolaldehyde. Notably, the pertinent selection of the aldolase variant provides control of the sugar size. The stereochemical outcome of the addition was also altered to allow the synthesis of L-glucose and related derivatives. Such engineered biocatalysts may offer new routes for the straightforward synthesis of natural molecules and their analogues that circumvent the intricate enzymatic pathways forged by evolution.
Relative reactivities in the O-methylation of glucomannans: The influence of stereochemistry at C-2 and the solvent effect
Zhang, Yujia,Li, Jiebing,Lindstr?m, Mikael E.,Mischnick, Petra
, p. 172 - 179 (2015/02/19)
The main hemicellulose in softwood, glucomannan (GM), structurally resembles cellulose but has quite different physical and chemical properties. In addition to branching and original acetylation, the only other difference between these two β-1,4-linked gl
Probe sialidase substrate specificity using chemoenzymatically synthesized sialosides containing C9-modified sialic acid
Khedri, Zahra,Muthana, Musleh M.,Li, Yanhong,Muthana, Saddam M.,Yu, Hai,Cao, Hongzhi,Chen, Xi
, p. 3357 - 3359 (2012/05/04)
A library of α2-3- and α2-6-linked sialyl galactosides containing C9-modified sialic acids was synthesized from C6-modified mannose derivatives using an efficient one-pot three-enzyme system. These sialosides were used in a high-throughput sialidase substrate specificity assay to elucidate the importance of C9-OH in sialidase recognition. The Royal Society of Chemistry 2012.
SYNTHESIS AND N.M.R.-SPECTRAL ANALYSIS OF UNENRICHED AND -ENRICHED 5-DEOXYPENTOSES AND 5-O-METHYLPENTOSES
Snyder. Joseph R.,Serianni, Anthony S.
, p. 169 - 188 (2007/10/02)
Chemical methods are described for preparing unenriched and -enriched 5-deoxy- and 5-O-methyl-pentoses in the D or L configuration.The 1H-n.m.r.-spectra of these compounds have been interpreted, and the 13C n.m.r. spectra assigned with the aid of 2-D 13C-1H chemical-shift correlation spectroscopy.Tautomeric forms (furanoses, hydrate, and aldehyde) in solution in 2H2O have been quantified with the aid of -enriched derivatives.Spectra of 5-deoxypentoses, and methyl pentofuranosides have been compared, in order to assess the effect of 5-C-deoxygenation and 5-O-methylation on chemical shifts and coupling constants (1H-1H, 13C-1H, and 13C-13C) and on the pentofuranose conformations.
The galactan sulphate of the red alga Polysiphonia lanosa.
Batey,Turvey
, p. 133 - 143 (2007/10/07)
The structure of the galactan sulphate of P. lanosa has been established by a combination of methylation, treatment with alkali, and partial methanolysis of the alkali-treated polysaccharide to give derivatives of agarobiose. The polysaccharide belongs to the agar class, in which 3-linked derivatives of beta-D-galactose alternate with 4-linked derivatives of alpha-L-galactose in a repeating sequence. In addition to D-galactose itself, the 3-linked units include 6-O-methyl-D-galactose, D-galactose 6-sulphate, and a hitherto unreported unit, 6-O-methyl-D-galactose 4-sulphate. The 4-linked units include L-galactose 6-sulphate, 2-O-methyl-L-galactose 6-sulphate, and 3,6-anhydro-L-galactose.
