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Escherichia coli K-12 substr. MG1655 Compound: 6-diazo-5-oxonorleucine

Systematic Name: Norleucine, 6-diazo-5-oxo-

Synonyms: DON, diazooxonorleucine, 6-diazo-5-oxo-L-norleucine

Chemical Formula: C6H10N3O3

Molecular Weight: 172.16 Daltons

Monoisotopic Molecular Weight: 172.0722162029 Daltons

SMILES: C(=[N+]=N)C(=O)CCC(C([O-])=O)[N+]

InChI: InChI=1S/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5,8H,1-2,7H2/p+1

InChIKey: InChIKey=LHGVYNDAWRBWGL-UHFFFAOYSA-O

Unification Links: CAS:764-17-0 , PubChem:25246179

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -121.35

Enzymes inhibited by 6-diazo-5-oxonorleucine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: L-glutamine:D-fructose-6-phosphate aminotransferase [Ghosh60, Badet87, Comment 1]

Inhibitor (Irreversible) of: xanthosine-5'-phosphate:L-glutamine amido-ligase (AMP-forming) [Patel77, Chittur01] , xanthosine-5'-phosphate:ammonia ligase (AMP-forming) [Patel77] , glutaminase [Hartman73, Hartman68, Comment 2]

Inhibitor (Mechanism unknown) of: amidophosphoribosyl transferase [Messenger79] , 4-amino-4-deoxychorismate synthase [Roux92, Comment 3] , carbamoyl phosphate synthetase [Helmward89, Khedouri66]


References

Badet87: Badet B, Vermoote P, Haumont PY, Lederer F, LeGoffic F (1987). "Glucosamine synthetase from Escherichia coli: purification, properties, and glutamine-utilizing site location." Biochemistry 1987;26(7);1940-8. PMID: 3297136

Badet88: Badet B, Vermoote P, Le Goffic F (1988). "Glucosamine synthetase from Escherichia coli: kinetic mechanism and inhibition by N3-fumaroyl-L-2,3-diaminopropionic derivatives." Biochemistry 1988;27(7);2282-7. PMID: 3132968

Chittur01: Chittur SV, Klem TJ, Shafer CM, Davisson VJ (2001). "Mechanism for acivicin inactivation of triad glutamine amidotransferases." Biochemistry 40(4);876-87. PMID: 11170408

Ghosh60: Ghosh S, Blumenthal HJ, Davidson E, Roseman S (1960). "Glucosamine Metabolism V. Enzymatic synthesis of glucosamine 6-phosphate." J Biol Chem 1960;235(5):1265-1273. PMID: 13827775

Hartman68: Hartman SC (1968). "Glutaminase of Escherichia coli. I. Purification and general catalytic properties." J Biol Chem 1968;243(5);853-63. PMID: 4966660

Hartman73: Hartman SC, McGrath TF (1973). "Glutaminase A of escherichia coli. Reactions with the substrate analogue, 6-diazo-5-oxonorleucine." J Biol Chem 1973;248(24);8506-10. PMID: 4587126

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

Khedouri66: Khedouri E, Anderson PM, Meister A (1966). "Selective inactivation of the glutamine binding site of Escherichia coli carbamyl phosphate synthetase by 2-amino-4-oxo-5-chloropentanoic acid." Biochemistry 1966;5(11);3552-7. PMID: 5339592

Messenger79: Messenger LJ, Zalkin H (1979). "Glutamine phosphoribosylpyrophosphate amidotransferase from Escherichia coli. Purification and properties." J Biol Chem 1979;254(9);3382-92. PMID: 372191

Patel77: Patel N, Moyed HS, Kane JF (1977). "Properties of xanthosine 5'-monophosphate-amidotransferase from Escherichia coli." Arch Biochem Biophys 1977;178(2);652-61. PMID: 189701

Roux92: Roux B, Walsh CT (1992). "p-aminobenzoate synthesis in Escherichia coli: kinetic and mechanistic characterization of the amidotransferase PabA." Biochemistry 1992;31(30);6904-10. PMID: 1637823


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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