Abstract
N-Medium-and long-chain acyl-L-amino acids were enzymatically synthesized from the corresponding L-amino acids and fatty acids using a reverse hydrolysis. Enzymes that are suitable for the synthetic reaction of N-acyl-L-amino acids were screened on the basis of hydrolytic activity toward N-lauroyl-L-glutamic acid as an indicator. Acylase I from pig kidney (EC 3.5.1.14) showed the highest N-acyl-L-amino acid hydrolytic activity among 57 commercially available enzymes tested. Acylase I effectively catalyzed the synthesis of N-lauroyl-L-amino acids except for N-lauroyl-L-proline and N-lauroyl-L-tyrosine in a glycerol-water system. Under the optimized reaction conditions, N-lauroyl-L-arginine and N-lauroyl-L-glutamic acid were obtained in conversions of 82 and 44%, respectively. The equilibrium constants calculated from the conversion obtained were 5.6, 15.4, 18.0, and 39.4 for the syntheses of N-lauroyl-L-glutamic acid, Nα-lauroyl-L-lysine, N-lauroyl-L-glutamine, and N-lauroyl-L-methionine, respectively. N-Acyl-L-arginines with myristic acid and palmitic acid as the fatty acid were also synthesized using acylase I.
| Original language | English |
|---|---|
| Pages (from-to) | 41-46 |
| Number of pages | 6 |
| Journal | JAOCS, Journal of the American Oil Chemists' Society |
| Volume | 79 |
| Issue number | 1 |
| Publication status | Published - Jan 2002 |
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Keywords
- Acylase I
- Enzymatic synthesis
- N-acyl-L-amino acid
- Pig kidney
ASJC Scopus subject areas
- Food Science
- Chemistry (miscellaneous)
Cite this
Enzymatic synthesis of N-acyl-L-amino acids in a glycerol-water system using acylase I from pig kidney. / Wada, Eiko; Handa, Masato; Imamura, Koreyoshi; Sakiyama, Takaharu; Adachi, Shuji; Matsuno, Ryuichi; Nakanishi, Kazuhiro.
In: JAOCS, Journal of the American Oil Chemists' Society, Vol. 79, No. 1, 01.2002, p. 41-46.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Enzymatic synthesis of N-acyl-L-amino acids in a glycerol-water system using acylase I from pig kidney
AU - Wada, Eiko
AU - Handa, Masato
AU - Imamura, Koreyoshi
AU - Sakiyama, Takaharu
AU - Adachi, Shuji
AU - Matsuno, Ryuichi
AU - Nakanishi, Kazuhiro
PY - 2002/1
Y1 - 2002/1
N2 - N-Medium-and long-chain acyl-L-amino acids were enzymatically synthesized from the corresponding L-amino acids and fatty acids using a reverse hydrolysis. Enzymes that are suitable for the synthetic reaction of N-acyl-L-amino acids were screened on the basis of hydrolytic activity toward N-lauroyl-L-glutamic acid as an indicator. Acylase I from pig kidney (EC 3.5.1.14) showed the highest N-acyl-L-amino acid hydrolytic activity among 57 commercially available enzymes tested. Acylase I effectively catalyzed the synthesis of N-lauroyl-L-amino acids except for N-lauroyl-L-proline and N-lauroyl-L-tyrosine in a glycerol-water system. Under the optimized reaction conditions, N-lauroyl-L-arginine and N-lauroyl-L-glutamic acid were obtained in conversions of 82 and 44%, respectively. The equilibrium constants calculated from the conversion obtained were 5.6, 15.4, 18.0, and 39.4 for the syntheses of N-lauroyl-L-glutamic acid, Nα-lauroyl-L-lysine, N-lauroyl-L-glutamine, and N-lauroyl-L-methionine, respectively. N-Acyl-L-arginines with myristic acid and palmitic acid as the fatty acid were also synthesized using acylase I.
AB - N-Medium-and long-chain acyl-L-amino acids were enzymatically synthesized from the corresponding L-amino acids and fatty acids using a reverse hydrolysis. Enzymes that are suitable for the synthetic reaction of N-acyl-L-amino acids were screened on the basis of hydrolytic activity toward N-lauroyl-L-glutamic acid as an indicator. Acylase I from pig kidney (EC 3.5.1.14) showed the highest N-acyl-L-amino acid hydrolytic activity among 57 commercially available enzymes tested. Acylase I effectively catalyzed the synthesis of N-lauroyl-L-amino acids except for N-lauroyl-L-proline and N-lauroyl-L-tyrosine in a glycerol-water system. Under the optimized reaction conditions, N-lauroyl-L-arginine and N-lauroyl-L-glutamic acid were obtained in conversions of 82 and 44%, respectively. The equilibrium constants calculated from the conversion obtained were 5.6, 15.4, 18.0, and 39.4 for the syntheses of N-lauroyl-L-glutamic acid, Nα-lauroyl-L-lysine, N-lauroyl-L-glutamine, and N-lauroyl-L-methionine, respectively. N-Acyl-L-arginines with myristic acid and palmitic acid as the fatty acid were also synthesized using acylase I.
KW - Acylase I
KW - Enzymatic synthesis
KW - N-acyl-L-amino acid
KW - Pig kidney
UR - http://www.scopus.com/inward/record.url?scp=0036193392&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036193392&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0036193392
VL - 79
SP - 41
EP - 46
JO - Oil & Soap
JF - Oil & Soap
SN - 0003-021X
IS - 1
ER -