Nopaline

Nopaline
Stereo, skeletal formula of nopaline
Stereo, skeletal formula of nopaline
Names
IUPAC name
(2R)-2-[[(1S)-1-Carboxy-4-(diaminomethylideneamino)butyl]amino]pentanedioic acid
Other names
N2-(D-1,3-Dicarboxypropyl)-L-arginine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C11H20N4O6/c12-11(13)14-5-1-2-6(9(18)19)15-7(10(20)21)3-4-8(16)17/h6-7,15H,1-5H2,(H,16,17)(H,18,19)(H,20,21)(H4,12,13,14)/t6-,7+/m0/s1 checkY
    Key: LMKYZBGVKHTLTN-NKWVEPMBSA-N checkY
  • C(C[C@@H](C(=O)O)N[C@H](CCC(=O)O)C(=O)O)CN=C(N)N
Properties
C11H20N4O6
Molar mass 304.303 g·mol−1
Related compounds
Related opines
 Octopine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nopaline is a chemical compound derived from the amino acids glutamic acid and arginine. It is classified as an opine. Ti plasmids are classified on the basis of the different types of opines they produce.[1] These may be nopaline plasmids, octopine plasmids and agropine plasmids. These opines are condensation products of amino acids and keto acids or may be derived from sugars. The opines are used as carbon and nitrogen sources and metabolized by Agrobacterium.

Biosynthesis

The enzyme D-nopaline dehydrogenase, also called nopaline synthase, produces or degrades nopaline by catalyzing the chemical reaction

2D representation of the chemical structure of Nopaline .
Nopaline
+ NADP+
 
 
H2O
H+
Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left
H2O
H+
 
2D representation of the chemical structure of Arginine .
Arginine
+ NADPH +
 
2D representation of the chemical structure of α-Ketoglutaric acid .
α-Ketoglutaric acid


Nopaline is a combination of the amino acid L-arginine and α-ketoglutaric acid.[2]

References

  1. ^ Depicker, A.; Stachel, S.; Dhaese, P.; Zambryski, P.; Goodman, H. M. (1982). "Nopaline synthase: Transcript mapping and DNA sequence". Journal of Molecular and Applied Genetics. 1 (6): 561–73. PMID 7153689.
  2. ^ Kemp JD, Sutton DW, Hack E (1979). "Purification and characterization of the crown gall specific enzyme nopaline synthase". Biochemistry. 18 (17): 3755–60. doi:10.1021/bi00584a017. PMID 476084.

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