A novel type of spiro compound formed by oxidative cross coupling of methyl sinapate with a syringyl lignin model compound.: A model system for the β-1 pathway in lignin biosynthesis

被引:25
作者
Setälä, H [1 ]
Pajunen, A [1 ]
Rummakko, P [1 ]
Sipilä, J [1 ]
Brunow, G [1 ]
机构
[1] Univ Helsinki, Dept Chem, Organ Chem Lab, FIN-00014 Helsinki, Finland
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 04期
关键词
D O I
10.1039/a808884e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidative coupling of methyl (E)-sinapate with 1(4-hydroxy-3,5-dimethoxyphenyl)ethanol a syringyl lignin model compound, was carried out with hydrogen peroxide catalyzed by horseradish peroxidase. The main product was a cyclohexadienone spiro compound of a novel type. Mild acidolysis caused the loss of one side chain and yielded a dimeric compound with a 1,2-diarylpropane structure. This is the first example of the formation of this;structural type by oxidative coupling in vitro.
引用
收藏
页码:461 / 464
页数:4
相关论文
共 20 条
[1]   INVESTIGATION OF THE ACID-CATALYZED ALKYLATION OF LIGNINS BY MEANS OF NMR SPECTROSCOPIC METHODS [J].
ADLER, E ;
BRUNOW, G ;
LUNDQUIST, K .
HOLZFORSCHUNG, 1987, 41 (04) :199-207
[2]   Labelling of a lignin from suspension cultures of Picea abies [J].
Brunow, G ;
Ämmälahti, E ;
Niemi, T ;
Sipilä, J ;
Simola, LK ;
Kilpeläinen, I .
PHYTOCHEMISTRY, 1998, 47 (08) :1495-1500
[3]   OXYZIMTALKOHOLE UND IHRE DEHYDRIERUNGS-POLYMERISATE [J].
FREUDENBERG, K ;
HUBNER, HH .
CHEMISCHE BERICHTE-RECUEIL, 1952, 85 (12) :1181-1191
[4]  
FREUDENBERG K, 1968, CONSTITUTION BIOSYNT, V2
[5]   FREE-RADICAL COMBINATION REACTIONS INVOLVING PHENOXYL RADICALS [J].
JONSSON, M ;
LIND, J ;
REITBERGER, T ;
ERIKSEN, TE ;
MERENYI, G .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (31) :8229-8233
[6]   APPLICATION OF 2-DIMENSIONAL NMR-SPECTROSCOPY TO WOOD LIGNIN STRUCTURE DETERMINATION AND IDENTIFICATION OF SOME MINOR STRUCTURAL UNITS OF HARDWOOD AND SOFTWOOD LIGNINS [J].
KILPELAINEN, I ;
SIPILA, J ;
BRUNOW, G ;
LUNDQUIST, K ;
EDE, RM .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1994, 42 (12) :2790-2794
[7]   HETEROGENEOUS DISTRIBUTION OF DIARYLPROPANE STRUCTURES IN SPRUCE LIGNINS [J].
LAPIERRE, C ;
POLLET, B ;
MONTIES, B .
PHYTOCHEMISTRY, 1991, 30 (02) :659-662
[8]  
LUNDQUIST K, 1965, TETRAHEDRON LETT, P2131, DOI 10.1016/S0040-4039(00)90166-7
[9]   ON THE OCCURRENCE OF BETA-1 STRUCTURES IN LIGNINS [J].
LUNDQUIST, K .
JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, 1987, 7 (02) :179-185
[10]   SYNTHESIS OF 3,4,5-TRIMETHOXYBENZALDEHYDE [J].
MANCHAND, PS ;
BELICA, PS ;
WONG, HS .
SYNTHETIC COMMUNICATIONS, 1990, 20 (17) :2659-2666