Nopaline

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
CAS Number	22350-70-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17249;
ChemSpider	19976727;
KEGG	C01682;
PubChem CID	108012;
UNII	QJ8EP5F7X8 ;
CompTox Dashboard (EPA)	DTXSID20945005;
	InChI 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 Key: LMKYZBGVKHTLTN-NKWVEPMBSA-N ;
	SMILES C(C[C@@H](C(=O)O)N[C@H](CCC(=O)O)C(=O)O)CN=C(N)N;
Properties
Chemical formula	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). Infobox references

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

H₂O

H⁺

H₂O

H⁺

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

^ 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.
^ 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.