The Adsorption Equilibria of <scp>Dl</scp>-Mandelic Acid on Starch in an Aqueous Phase

Ohara, Masaaki; Chen, Chau-Yang; Kwan, Takao

doi:10.1246/bcsj.39.137

Cited by 7 publications

(1 citation statement)

References 6 publications

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“…It should be noted that dl -mandelic acid is a readily available feedstock from glucose. 36 As shown in Fig. 2a, the partial oxidation of the alcohol group in dl -mandelic acid will produce phenylglyoxylic acid as the desired product, while further oxidative cleavage of the carboxylic group will yield benzoic acid, an undesirable side product.…”

Section: Resultsmentioning

confidence: 99%

Electrosynthesis of amino acids from biomass-derived α-hydroxyl acids

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Electrosynthesis of amino acids from biomass-derived α-hydroxyl acids

et al. 2022

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Synthesis of membranes having a saccharide side chain and their optical resolution properties for d‐/l‐ glucose mixtures

Nakagawa

Toyokawa

Abe

et al. 1994

Macromolecular Symposia

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The objective of the present investigation is to synthesize new polymeric membranes having a saccharide in the side chain and to clarify the specific affinity of the saccharide chains. During this study chloromethylated polysulfone (CM‐PSF), poly(chloromethylated styrene) (P‐CM‐St), poly(methyl methacrylate) (PMMA), and chlororethylated poly(γ ‐methyl L‐glutamate) (CE‐PMLG) as synthetic polymers along with an equal mixture of α‐D‐2‐deoxy‐2‐aminoglucopyranosyl‐(1'→6) ‐D‐sorbitol and mannitol (AGP) as saccharides were used. PMMA+AGP and CE‐PMLG+AGP membranes showed the highest permeability of D‐glucose in sugars (molecular weight = 180.16), although the CM‐PSP+AGP and P‐CM‐St+AGP membranes showed less permeability. The reason for the high permeability of D‐glucose is the high partition coefficient of D‐glucose, which may come from an interaction between the AGP terminating D‐glucose structure and D‐glucose as the solute. The optical resolution could be done by the difference between the D‐ and L‐glucose permeation rates from an equimolar mixture of D‐glucose and L‐glucose.

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Optical resolution of mandelic acid derivatives by column chromatography on crosslinked cyclodextrin gels

Harada

Furue

Nozakura

1978

J. Polym. Sci. Polym. Chem. Ed.

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Crosslinked α‐ and β‐cyclodextrin gels (α‐CD‐E and β‐CD‐E) were used for the chromatographic resolution of racemic mandelic acid and its derivatives. β‐CD‐E bound L‐(+)‐isomers preferentially over D‐(−)‐isomers and resolved DL‐methyl mandelate to give a D‐(−)‐isomer of 100% optical purity in the first fraction. Mandelic acid, ethyl mandelate, and O‐methylated mandelic acid yielded resolutions of 65–83% in initial fractions. α‐CD‐E, on the contrary, bound D‐(−)‐isomers more strongly than L‐(+)‐isomers, resolving DL‐methyl mandelate to a smaller extent than β‐CD‐E. Binding of DL‐mandelic acid and DL‐methyl mandelate on β‐CD‐E was studied quantitatively by the equilibrium method. β‐CD‐E has a similar binding capacity to starch with 1:1 stoichiometry but bound much more strongly than starch. β‐CD‐E has the same mode of selectivity as starch for the asymmetric binding of the mandelic acid derivatives, but α‐CD‐E has a reverse selectivity to β‐CD‐E and starch.

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The Adsorption Equilibria of Dl-Mandelic Acid on Starch in an Aqueous Phase

Cited by 7 publications

References 6 publications

Electrosynthesis of amino acids from biomass-derived α-hydroxyl acids

Electrosynthesis of amino acids from biomass-derived α-hydroxyl acids

Synthesis of membranes having a saccharide side chain and their optical resolution properties for d‐/l‐ glucose mixtures

Optical resolution of mandelic acid derivatives by column chromatography on crosslinked cyclodextrin gels

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