Formose Reaction Controlled by a Copolymer of N,N-Dimethylacrylamide and 4-Vinylphenylboronic Acid

被引:5
作者
Michitaka, Tomohiro [1 ]
Imai, Toru [1 ]
Hashidzume, Akihito [1 ]
机构
[1] Grad Osaka Univ, Dept Macromol Sci, Osaka 5600043, Japan
关键词
formose reaction; boronic acid compounds; N; N-dimethylacrylamide; 4-vinylphenylboronic acid copolymer; phenylboronic acid; monosaccharides; sugar alcohols; SELECTIVE FORMATION; POTENTIOMETRIC ANALYSIS; 2-STEP SYNTHESIS; ALDOL REACTIONS; SUGARS; OLIGOSACCHARIDES; POLYMERS; TRIOSE;
D O I
10.3390/polym9110549
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The formose reaction is an oligomerization of formaldehyde under basic conditions, which produces a complicated mixture of monosaccharides and sugar alcohols. Selective formation of useful monosaccharides by the formose reaction has been an important challenge. In this study, we have investigated the formose reaction controlled by N,N-dimethylacrylamide/4-vinylphenylboronic acid copolymer (pDMA/VBA) and phenylboronic acid (PBA) because boronic acid compounds form esters with polyols, e.g., monosaccharides and sugar alcohols. We obtained time-conversion data in the presence of these boronic acid compounds, and characterized the products by liquid chromatography-mass spectroscopy and NMR measurements. pDMA/VBA and PBA decelerated the formose reaction because of the formation of boronic acid esters with products. It is noteworthy that the formose reaction in the presence of pDMA/VBA and PBA formed favorably six- and seven-carbon branched monosaccharides and sugar alcohols.
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页数:11
相关论文
共 45 条
[1]   THE SYNTHESIS OF CARBOHYDRATE-DERIVATIVES FROM ACYCLIC PRECURSORS [J].
AGER, DJ ;
EAST, MB .
TETRAHEDRON, 1993, 49 (26) :5683-5765
[2]  
Alberts B., 2014, Molecular Biology of the Cell: Sixth International Student Edition
[3]   Chemical glycobiology [J].
Bertozzi, CR ;
Kiessling, LL .
SCIENCE, 2001, 291 (5512) :2357-2364
[4]  
BRESLOW R, 1959, TETRAHEDRON LETT, P22
[5]   L-amino acids catalyze the formation of an excess of D-glyceraldehyde, and thus of other D sugars, under credible prebiotic conditions [J].
Breslow, Ronald ;
Cheng, Zhan-Ling .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (13) :5723-5725
[6]   Synthesis and Applications of Boronic Acid-Containing Polymers: From Materials to Medicine [J].
Brooks, William L. A. ;
Sumerlin, Brent S. .
CHEMICAL REVIEWS, 2016, 116 (03) :1375-1397
[7]  
Butlerow A., 1861, Justus Liebigs Ann. Chem, V120, P295, DOI DOI 10.1002/JLAC.18611200308
[8]   Catalytic Formation of Monosaccharides: From the Formose Reaction towards Selective Synthesis [J].
Delidovich, Irina V. ;
Simonov, Alexandr N. ;
Taran, Oxana P. ;
Parmon, Valentin N. .
CHEMSUSCHEM, 2014, 7 (07) :1833-1846
[9]   INFRARED SPECTRA OF PHEYNLBORONIC ACID (NORMAL AND DEUTERATED) AND DIPHENYL PHENYLBORONATE [J].
FANIRAN, JA ;
SHURVELL, HF .
CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (12) :2089-&
[10]  
Hall D, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, pXV