Synthesis of a reaction intermediate analogue of biotin-dependent carboxylases via a selective derivatization of biotin

Organic Letters

Volumn 1, Issue 1, 1999, Pages 99-102

  Amspacher, David R ^a   Blanchard, Carol Z ^a   Fronczek, Frank R ^a   Saraiva, Marcelo C ^a   Waldrop, Grover L ^a   Strongin, Robert M ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AVIDIN; BIOTIN; BIOTIN CARBOXYLASE; LIGASE;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; KINETICS; SYNTHESIS;

AVIDIN; BIOTIN; CARBON-NITROGEN LIGASES; KINETICS;

EID: 0033565009     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990026z     Document Type: Article

References (24)

1. Vitamins and Coenzymes; Wagner, A. F., Folkers, K., Eds.; Wiley: New York, 1964; pp 138-159.
2. Good, H. G.; Barden, R. E. Annu. Rev. Biochem. 1977, 46, 385-413.
3. Blanchard, C. Z.; Lee, Y. M.; Frantom, P. A.; Waldrop, G. L. Biochemistry 1999, 38, 3393-3400.
4. Guchhait, R. B.; Polakis, S. E.; Hollis, D.; Fenselau, C.; Lane, M. D. J. Biol. Chem. 1974, 249, 6646-6656.
5. Knowles, J. R. Annu. Rev. Biochem. 1989, 58, 195-221.
6. (a) Diamonds, E. P.; Christopoulos, T. K. Clin. Chem. 1991, 37, 625-636.
7. (b) Methods in Enzymology; Wilchek, M., Edward, E. A., Eds.; Academic Press: New York, 1990; Vol. 184.
8. (a) Launer, H. F.; Fraenkel-Conrat, H. J. Biol. Chem. 1951, 193, 125-132.
9. (b) Green, N. M. Biochem. J. 1963, 89, 585-591.
10. (c) Green, N. M. Adv. Protein Chem. 1975, 29, 85-133.
11. Weber, P. C.; Ohlendorf, D. H.; Wendoloski, J. J.; Salemme, F. R. Science 1989, 243, 85-88.
12. Knappe, J.; Ringelmann, E.; Lynen, F. Biochem. Z. 1961, 335, 168-176.
13. Berkessel, A.; Breslow, R. Bioorg. Chem. 1986, 14, 249-261.
14. +).
15. +).
16. +).
17. 3, Z = 2, colorless, T = 299 K, R = 0.096, GOF = 4.753. Displacement parameters of the benzyl ester and phosphonate groups are large; low-temperature data collection is planned.
18. +).
19. +).
20. Lane, M. D.; Moss, J.; Polakis, S. E. Curr. Top. Cell Regul. 1974, 8, 139-195.
21. Li, S. J.; Cronan, J. E., Jr. J. Biol. Chem. 1992, 267, 855-863.
22. Kondo, H.; Shiratsuchi, K.; Yoshimoto, T.; Masuda, T.; Kitazono, A.; Tsuru, D.; Anai, M.; Sekiguchi, M.; & Tanabe, T. Proc. Natl. Acad. Sci. USA 1991, 88, 9730-9733.
23. Waldrop, G. L.; Rayment, I.; Holden, H. M. Biochemistry 1994, 33, 10249-10256.
24. Tipton, P. A.; Cleland, W. W. Biochemistry 1988, 27, 4317-4325.