Chemoenzymatic synthesis of Galα1-3Gal, Galα1-3Galβ1-4GlcNAc, and their PEG-conjugates

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 3, 1997, Pages 255-258

  Matsuo, Ichiro ^a   Fujimoto, Hiroshi ^a   Isomura, Megumi ^a   Ajisaka, Katsumi ^a  

^a MEIJI DAIRIES CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA GALACTOSIDASE; EPITOPE; MACROGOL; MACROGOL DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CONJUGATION; ENZYME ACTIVITY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031552087     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00017-6     Document Type: Article

References (14)

1. 1. D. K. C. Cooper, E. Koren, R. Oriol, Immunological Reviews, 1994, 31-58.
2. 2. M. S. Sandrin, H. A. Vaughan, P. L. Dabkowski, and I. F. C. Mckenzie, Proc. Natl. Acad. Sci. USA., 1993, 90, 11391-11395.
3. 3. D. K. C. Cooper, E. Coren, R. Oriol, Xeno, 1994, 2, 22-25.
4. 4. K. G. I. Nilsson, Carbohydr. Res., 1987, 167, 95-103.
5. 5. Activated PEG, commercial name of Activated PEG-2, was purchased from Seikagaku-Kogyo Co. (Osaka, Japan).
6. 6. Galα1-3Gal-pNP was synthesized according to the method of Nilsson. We succeeded to increase the yield to about 1.7 times of Nilsson's report by the improvement of the reaction condition. Gal-pNP (1.0g) was dissolved in 4ml of 0.1M potassium phosphate buffer (pH 6.0) containing 30% DMF, the solution was incubated for 4hrs at 37°C after the addition of 26.7 units of galactosidase from coffee beans. After the deactivation of enzyme by heating the solution in boiling water bath for 5 minutes, the solution was applied to Sephadex G-15 column (2.5cmφ × 100cm). By the elution with water, 169.2mg of Galα1-3Gal-pNP was isolated and 28.6mg of Galα1-2Gal-pNP was also obtained as a by-product.
7. 7. K. Fukase, T. Yasukochi, Y. Nakai, and S. Kusumoto, Tetrahedron Letters, 1996, 37, 3343-3344.
8. 3). Non-reducing end galactose residue was named as Gal'. The ratio of the integral intensity of the signals at δ7.55 and δ3.40 was 1:3.
9. 9. The calculation of the yield was based on that the average molecular weight of the activated PEG as 10,000 dalton.
10. 10. T. Ogawa and S. Nakabayashi, Carbohydr, Res., 1981, 97, 81-86.
11. 3); δ100.438(Gal, C-1), 97.472(GlcNAc, C-1), 93.964(Gal', C-1).
12. 12. O. Kanie, S. C. Crawley, M. M. Palcic, and O. Hindsgaul, Carbohydr. Res., 1993, 243, 139-164.
13. 3); δ100.586(Gal, C-1), 95.511(GlcNAc, C-1), 93.933(Gal', C-1).
14. 3).