First synthesis of both enantiomers of the biotin vitamer 8-amino-7-oxopelargonic acid

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 985-988

  Lucet, Denis ^a   Le Gall, Thierry ^a   Mioskowski, Charles ^a   Ploux, Olivier ^b   Marquet, Andrée ^b  

^a CEA SACLAY   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

8 AMINO 7 OXONONANOIC ACID; BIOTIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; FUNGUS GROWTH; PRIORITY JOURNAL; REACTION ANALYSIS; SACCHAROMYCES CEREVISIAE;

EID: 0029938042     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00098-5     Document Type: Article

References (25)

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3. Baldet, P.; Gerbling, H.; Axiotis, S.; Douce, R. Eur. J. Biochem. 1993, 217, 479-485.
4. 20 that rac-8-amino-7-oxopelargonic acid underwent a 3-deuterium exchange at the α-carbonyl position using 6M DCl at reflux, indicating that racemisation occured under these conditions.
5. 20 that rac-8-amino-7-oxopelargonic acid underwent a 3-deuterium exchange at the α-carbonyl position using 6M DCl at reflux, indicating that racemisation occured under these conditions.
6. 3, no optical activity was reported.
7. This enzyme catalyzes the conversion of 8-amino-7-oxopelargonic acid to 7,8-diaminopelargonic acid (DAPA).
8. Chakravarty, P. K.; Combs, P.; Roth, A.; Greenlee, W. J. Tetrahedron Lett. 1987, 28, 611-612.
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10. 3. By this technique, a 2% precision was assumed.
11. 3N).
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13. Koskinen, A. M. P.; Koskinen, P. M. Synlett, 1993, 501-502.
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15. D - 14.2 (c 2.4, MeOH).
16. 5 requires C, 58.52, H, 8.77, N, 4.87, O, 27.84%.
17. 3 requires C, 48.32, H, 8.11, N, 6.26%.
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20. 3 can not be used to determine the e.e. since no split signal was observed for a sample of the racemic compound ; HPLC analysis of (R)-1-(1-naphthyl)ethyl isocyanate-derived adducts of methyl esters of synthesized (+) or (-)-6 led to inconsistent results with e.e. varying from 46 to 60%. Some racemisation may have occured during one of the steps required to carry out this analysis.
21. Genghof, D.S.; Partridge, C.W.H.; Carpenter, F.H. Arch. Biochem. 1948, 17, 413-420.
22. Gaudry, M.; Ploux, O. Modern Chromatographic Analysis of Vitamins; De Leenheer, A. P.; Lambert, W.E.; Nelis, H.J. Eds.; M. Dekker : New York, 1992, 2nd ed., pp 441-467.
23. Ploux, O.; Marquet, A. Eur. J. Biochem. 1996 in press.
24. Oshugi, M.; Imanishi, Y. J. Nutr. Sci. Vitaminol. 1985, 31, 563-572.
25. Ploux, O.; Marquet, A. Biochem. J. 1992, 283, 327-331.