Hydrolysis of cyclic ureas under microwave irradiation: Synthesis and characterization of 7,8-diaminopelargonic acid

Synthetic Communications

Volumn 37, Issue 16, 2007, Pages 2633-2639

  Vasanthakumar, Ganga Ramu ^a   Bhor, Vikrant M ^a   Surolia, Avadhesha ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

7,8 diaminopelargonic acid; Acid hydrolysis; Cyclic urea; d desthiobiotin; Microwave irradiation

Indexed keywords

7,8 DIAMINOPELARGONIC ACID; BIOTIN; DIAMINE DERIVATIVE; HYDROCHLORIC ACID; NONANOIC ACID; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; BIOSYNTHESIS; HYDROLYSIS; MICROWAVE RADIATION; SYNTHESIS;

EID: 34547934799     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701464951     Document Type: Article

References (18)

1. Marquet, A.; Tse Sum Bui, B.; Florentin, D. Biosynthesis of biotin and lipoic acid. Vitam. Horm. 2001, 61, 51-101.
2. Schneider, G.; Lindqvist, Y. Structural enzymology of biotin biosynthesis. FEBS Lett. 2001, 495, 7-11.
3. Nudelman, A.; Nudelman, A.; Macrovici-Mizrahi, D.; Flint, D. The synthesis of the vitamers of biotin. Bioorg. Chem. 1998, 26, 157-168.
4. du Vigneaud, V.; Melville, D. B.; Folkers, K.; Wolf, D. E.; Mozingo, R.; Keresztesy, J. C.; Harris, S. A. The structure of biotin: A study of desthiobiotin. J. Biol. Chem. 1942, 146, 475-485.
5. (a) Dunn, P. J.; Haner, R.; Rapoport, H. Stereoselective synthesis of 2,3-diamino acids: 2,3-Diamino-4-phenylbutanoic acid. J. Org. Chem. 1990, 55, 5017-5025;
6. (b) Jones, R. C. F.; Schofield, J. 2-Methyl-4,5-dihydroimidazole as a doubly nucleophilic unit: Preparation of dihydroimidazole azaprostanoids. J. Chem. Soc., Perkin Trans. 1 1990, 375-383.
7. (a) Hoffmann, K.; Melville, D. B.; du Vigneaud, V. Characterization of the functional groups of biotin. J. Biol. Chem. 1941, 141, 207-214;
8. (b) Jung, S.-H.; Kohn, H. A new reductive procedure for the preparation of vicinal diamines and monoamines. Tetrahedron Lett. 1984, 25, 399-402.
9. (a) Loupy, A. Microwaves in Organic Synthesis; Wiley-VCH: Weinheim, 2002;
10. (b) de la Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Microwaves in organic synthesis: Thermal and nonthermal microwave effects. Chem. Soc. Rev. 2005, 164-178;
11. (c) Kappe, C. O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 2004, 43, 6250-6280;
12. (d) Murray, J. K.; Gellman, S. H. Microwave-assisted parallel synthesis of a 14-helical beta-peptide library. J. Comb. Chem. 2006, 8, 58-65.
13. (a) Vasanthakumar, G. R.; Patil, B. S.; Suresh Babu, V. V. Microwave assisted facile synthesis of amino acid benzyl ester p-toluenesulphonate and hydrochloride salts. Lett. Peptide Sci. 2003, 9, 207-209;
14. (b) Patil, B. S.; Vasanthakumar, G. R.; Suresh Babu, V. V. Isocyanates of N-[(9-fluorenylmethyl)oxy]carbonyl (Fmoc) amino acids: Synthesis, isolation, characterization and application to the efficient synthesis of urea peptidomimetics. J. Org. Chem. 2003, 63, 7274-7280;
15. (c) Kumar, S.; Kapoor, M.; Surolia, N.; Surolia, A. One-step synthesis of novel antimicrobial 2-hydroxy diaryl ethers through domestic microwave heating. Synth. Commun. 2004, 34, 413-420.
16. Stoner, G. L.; Eisenberg, M. A. Biosynthesis of 7,8-diaminopelargonic acid from 7-keto-8-aminopelargonic acid and S-adenosyl-L-methionine: The kinetics of the reaction. J. Biol. Chem. 1975, 250, 4037-4043.
17. Bhor, V. M.; Dev, S.; Vasanthakumar, G. R.; Surolia, A. Spectral and kinetic characterization of 7,8-diaminopelargonic acid synthase from mycobacterium tuberculosis. IUMB Life 2006, 58, 225-233;
18. (b) Bhor, V. M.; Dev, S.; Vasanthakumar, G. R.; Kumar, P.; Sinha, S.; Surolia, A. Broad substrate stereospecificity of the Mycobacterium tuberculosis 7-keto-8-aminopelargonic acid synthase: Spectroscopic and kinetic studies. J. Biol. Chem. 2006, 281, 25076-25088.