3-Methylornithine

3-Methylornithine

Names
Other names 5-Aminoisoleucine
Identifiers
CAS Number	1224728-50-0
3D model (Jmol)	Interactive image
ChemSpider	26001508
InChI InChI=1S/C6H14N2O2/c1-4(2-3-7)5(8)6(9)10/h4-5H,2-3,7-8H2,1H3,(H,9,10)/t4-,5-/m1/s1 Key: HYUPFEBCCJWDJX-RFZPGFLSSA-N InChI=1/C6H14N2O2/c1-4(2-3-7)5(8)6(9)10/h4-5H,2-3,7-8H2,1H3,(H,9,10)/t4-,5-/m1/s1 Key: HYUPFEBCCJWDJX-RFZPGFLSBQ
SMILES C[C@H](CCN)[C@H](C(=O)O)N
Properties
Chemical formula	C6H14N2O2
Molar mass	146.19 g·mol−1
Appearance	White solid
Density	1.121 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3-Methylornithine is an amino acid with the formula H₂N(CH₂)₂CH(CH₃)CH(NH₂)CO₂H. This amino acid contains two stereogenic centers, but only one stereoisomer occurs in nature. It is produced from lysine by the action of the enzyme methylornithine synthase. The combination of lysine and 3-methylornithine, also mediated enzymatically, produces pyrrolysine, which, for a few organisms, is a "22nd" genetically coded amino acid.^[1][2]

Structure of pyrrolysine, which is biosynthesized from methylornithine and lysine

References

1. ↑ Gaston, Marsha A.; Jiang, Ruisheng; Krzycki, Joseph A. "Functional Context, Biosynthesis, and Genetic Encoding of Pyrrolysine" Current Opinion in Microbiology 2011, vol. 14, pp. 342-349. doi:10.1016/j.mib.2011.04.001
2. ↑ Quitterer, F.; Beck, P.; Bacher, A.; Groll, M., "Structure and Reaction Mechanism of Pyrrolysine Synthase (PylD)", Angew. Chem. Int. Ed. 2013, volume 52, pp. 7033-7037. doi:10.1002/anie.201301164