TY - JOUR
T1 - Enzymatic Kolbe-Schmitt reaction to form salicylic acid from phenol
T2 - Enzymatic characterization and gene identification of a novel enzyme, Trichosporon moniliiforme salicylic acid decarboxylase
AU - Kirimura, Kohtaro
AU - Gunji, Hiroaki
AU - Wakayama, Rumiko
AU - Hattori, Takasumi
AU - Ishii, Yoshitaka
N1 - Funding Information:
This study was supported in part by the Global-COE Program “Center for Practical Chemical Wisdom” from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan and by Waseda University Grant for Special Research Projects.
PY - 2010/4/2
Y1 - 2010/4/2
N2 - Salicylic acid decarboxylase (Sdc) can produce salicylic acid from phenol; it was found in the yeast Trichosporon moniliiforme WU-0401 and was for the first time enzymatically characterized, with the sdc gene heterologously expressed. Sdc catalyzed both reactions: decarboxylation of salicylic acid to phenol and the carboxylation of phenol to form salicylic acid without any byproducts. Both reactions were detected without the addition of any cofactors and occurred even in the presence of oxygen, suggesting that this Sdc is reversible, nonoxidative, and oxygen insensitive. Therefore, it is readily applicable in the selective production of salicylic acid from phenol, the enzymatic Kolbe-Schmitt reaction. The deduced amino acid sequence of the gene, sdc, encoding Sdc comprises 350 amino acid residues corresponding to a 40-kDa protein. The recombinant Escherichia coli BL21(DE3) expressing sdc converted phenol to salicylic acid with a 27% (mol/mol) yield at 30 °C for 9 h.
AB - Salicylic acid decarboxylase (Sdc) can produce salicylic acid from phenol; it was found in the yeast Trichosporon moniliiforme WU-0401 and was for the first time enzymatically characterized, with the sdc gene heterologously expressed. Sdc catalyzed both reactions: decarboxylation of salicylic acid to phenol and the carboxylation of phenol to form salicylic acid without any byproducts. Both reactions were detected without the addition of any cofactors and occurred even in the presence of oxygen, suggesting that this Sdc is reversible, nonoxidative, and oxygen insensitive. Therefore, it is readily applicable in the selective production of salicylic acid from phenol, the enzymatic Kolbe-Schmitt reaction. The deduced amino acid sequence of the gene, sdc, encoding Sdc comprises 350 amino acid residues corresponding to a 40-kDa protein. The recombinant Escherichia coli BL21(DE3) expressing sdc converted phenol to salicylic acid with a 27% (mol/mol) yield at 30 °C for 9 h.
KW - Enzymatic Kolbe-Schmitt reaction
KW - Reversible decarboxylase
KW - Salicylic acid decarboxylase
KW - Selective production
KW - Trichosporon moniliiforme
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U2 - 10.1016/j.bbrc.2010.02.154
DO - 10.1016/j.bbrc.2010.02.154
M3 - Article
C2 - 20188702
AN - SCOPUS:77950228892
SN - 0006-291X
VL - 394
SP - 279
EP - 284
JO - Biochemical and Biophysical Research Communications
JF - Biochemical and Biophysical Research Communications
IS - 2
ER -