Monoacylation of 2-O-α-d-glucopyranosyl-l-ascorbic acid by protease in N,N-dimethylformamide with low water content

Carbohydrate Research

Volumn 345, Issue 12, 2010, Pages 1658-1662

  Tai, Akihiro ^a   Mori, Tasuku ^a   Kimura, Yuka ^b   Ito, Hideyuki ^b  

^a PREFECTURAL UNIVERSITY OF HIROSHIMA   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

2 O d Glucopyranosyl l ascorbic acid; N,N Dimethylformamide; Protease; Transacylation; Vinyl laurate; Water

Indexed keywords

L-ASCORBIC ACID; LAURATE; N ,N-DIMETHYLFORMAMIDE; PROTEASE; TRANSACYLATION;

BACTERIOLOGY; DIMETHYLFORMAMIDE; KETONES; ORGANIC ACIDS; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

WATER CONTENT;

2 O (6' O DODECANOYL ALPHA DEXTRO GLUCOPYRANOSYL)LEVO ASCORBIC ACID; 5 O DODECANOYL 2 O ALPHA DEXTRO GLUCOPYRANOSYL LEVO ASCORBIC ACID; 6 O DODECANOYL 2 O ALPHA DEXTRO GLUCOPYRANOSYL LEVO ASCORBIC ACID; ASCORBIC ACID DERIVATIVE; LAURIC ACID DERIVATIVE; LAURIC ACID VINYL ESTER; N,N DIMETHYLFORMAMIDE; PROTEINASE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; WATER CONTENT;

ACYLATION; ASCORBIC ACID; BIOCATALYSIS; CARBOHYDRATE SEQUENCE; FORMAMIDES; MOLECULAR CONFORMATION; PEPTIDE HYDROLASES; STEREOISOMERISM; WATER;

BACILLUS SUBTILIS;

EID: 77955473325     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2010.04.028     Document Type: Article

References (22)

1. I. Yamamoto, N. Muto, E. Nagata, T. Nakamura, and Y. Suzuki Biochim. Biophys. Acta 1035 1990 44 50
2. I. Yamamoto, N. Muto, K. Murakami, S. Suga, and H. Yamaguchi Chem. Pharm. Bull. 38 1990 3020 3023
3. H. Aga, M. Yoneyama, S. Sakai, and I. Yamamoto Agric. Biol. Chem. 55 1991 1751 1756
4. T. Mandai, M. Yoneyama, S. Sakai, N. Muto, and I. Yamamoto Carbohydr. Res. 232 1992 197 205
5. I. Yamamoto, S. Suga, Y. Mitoh, M. Tanaka, and N. Muto J. Pharmacobio-Dyn. 13 1990 688 695
6. I. Yamamoto, N. Muto, K. Murakami, and J. Akiyama J. Nutr. 122 1992 871 877
7. Y. Kumano, T. Sakamoto, M. Egawa, M. Tanaka, and I. Yamamoto Biol. Pharm. Bull. 21 1998 662 666
8. I. Yamamoto, A. Tai, Y. Fujinami, K. Sasaki, and S. Okazaki J. Med. Chem. 45 2002 462 468
9. A. Tai, D. Kawasaki, K. Sasaki, E. Gohda, and I. Yamamoto Chem. Pharm. Bull. 51 2003 175 180
10. A. Tai, S. Goto, Y. Ishiguro, K. Suzuki, T. Nitoda, and I. Yamamoto Bioorg. Med. Chem. Lett. 14 2004 623 627
11. M. Therisod, and A.M. Klibanov J. Am. Chem. Soc. 108 1986 5638 5640
12. S. Riva, J. Chopineau, A.P.G. Kieboom, and A.M. Klibanov J. Am. Chem. Soc. 110 1988 584 589
13. D. Kwoh, D.J. Pocalyko, A.J. Carchi, B. Harirchian, L.O. Hargiss, and T.C. Wong Carbohydr. Res. 274 1995 111 121
14. N.B. Bashir, S.J. Phythian, A.J. Reason, and S.M. Roberts J. Chem. Soc., Perkin Trans. 1 1995 2203 2222
15. A. Tai, S. Okazaki, N. Tsubosaka, and I. Yamamoto Chem. Pharm. Bull. 49 2001 1047 1049
16. P. Potier, A. Bouchu, J. Gagnaire, and Y. Queneau Tetrahedron: Asymmetry 12 2001 2409 2419
17. T. Raku, M. Kitagawa, H. Shimakawa, and Y. Tokiwa Biotechnol. Lett. 25 2003 161 166
18. N.R. Pedersen, R. Wimmer, R. Matthiesen, L.H. Pedersen, and A. Gessesse Tetrahedron: Asymmetry 14 2003 667 673
19. M. Ferrer, M.A. Cruces, M. Bernabé, A. Ballesteros, and F.J. Plou Biotechnol. Bioeng. 65 1999 10 16
20. Y. Watanabe, Y. Minemoto, S. Adachi, K. Nakanishi, Y. Shimada, and R. Matsuno Biotechnol. Lett. 22 2000 637 640
21. Y. Watanabe, Y. Miyawaki, S. Adachi, K. Nakanishi, and R. Matsuno J. Mol. Catal. B: Enzym. 10 2000 241 247
22. L. Tang, Z. Hao, M.M. Shehate, and Y. Sun Biotechnol. Appl. Biochem. 32 2000 35 39