Synthesis of Acids and Amino Acids by Selective Oxidation of Primary Hydroxyl Groups to Carboxylic acids in Sugars

Preferential oxidation of primary hydroxyls in unprotected sugars and sugar amino acids is reported using inexpensive and readily available reagents. This method offers a specific oxidation protocol for a variety of carbohydrates. The stereochemical integrity of the starting materials was preserved and a simple workup yielded the products in good yields with high purity. The procedure is compatible with base sensitive groups like Fmoc.  Both mono and disaccharides undergo oxidation regioselectively.

Download Full-text

ChemInform Abstract: OXIDATION WITH CHLORINE COMPLEXES, SPECIFIC OXIDATION OF SECONDARY HYDROXYL GROUPS IN THE PRESENCE OF PRIMARY HYDROXYL GROUPS IN POLYHYDRIC ALCOHOLS

Chemischer Informationsdienst ◽

10.1002/chin.197451474 ◽

1974 ◽

Vol 5 (51) ◽

pp. no-no

Author(s):

J. WICHA ◽

A. ZARECKI

Keyword(s):

Hydroxyl Groups ◽

Secondary Hydroxyl ◽

Polyhydric Alcohols ◽

Primary Hydroxyl ◽

Specific Oxidation

Download Full-text

The Preparation and Characterization of Starch Oxidized by Nitric Acid and its Properties of Calcium Complexing Capacity

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.652-654.1593 ◽

2013 ◽

Vol 652-654 ◽

pp. 1593-1596 ◽

Cited By ~ 1

Author(s):

Xue Chuan Wang ◽

Fei Hu Li ◽

Tao Tao Qiang

Keyword(s):

Nitric Acid ◽

Carboxylic Acids ◽

Hydroxyl Groups ◽

Oxidized Starch ◽

Complexing Capacity ◽

Primary Hydroxyl ◽

Ft Ir

The primary hydroxyl groups of Starch Oxidized by nitric acid to the corresponding carboxylic acids has been investigated. The structure of the Oxidized-Starch(OS) was characterized by FT-IR, 1HNMR and GPC. The predicated product was obtained from the results. Its application in calcium complexing capacity has been discussed. The calcium complexing capacity of OS may up to 119.39 mg/g. The data confirmed that the starch oxidized by nitric acid had excellent capacity of calcium complexing.

Download Full-text

Synthese furanoider Zuckeraminos¨auren ausgehend von fermentativ gewonnener 2-Oxo-D-gluconsäure / Synthesis of Furanoid Sugar Amino Acids Starting from Fermentatively Produced 2-Oxo-D-gluconic Acid

Zeitschrift für Naturforschung B ◽

10.1515/znb-2005-1109 ◽

2005 ◽

Vol 60 (11) ◽

pp. 1168-1174 ◽

Cited By ~ 3

Author(s):

Stephan Schmidt ◽

Horst Wilde ◽

Jens Hunger ◽

Dieter Sicker

Keyword(s):

Crystal Structure ◽

Amino Acids ◽

Amino Acid ◽

Gluconic Acid ◽

Crystal Structure Analysis ◽

The Other ◽

Hydroxyl Groups ◽

Sugar Amino Acids ◽

Other Substances ◽

Furanose Form

2-Oxo-D-gluconic acid obtained by fermentation of D-glucose was used as starting material for syntheses of amino acids. We trapped the carbohydrate in its furanoid configuration and synthesized an α- and an ω-amino acid. After deprotection of the hydroxyl groups the latter did not isomerize to the substituted piperidine (aza-sugar) as expected, but remained in the furanose form. The starting structure 2 was proven by crystal structure analysis. The conformational identification of the other substances was done by NMR measurements following known rules for furanoses.

Download Full-text