8019. Pyrrolysine

Nomenclature

CAS number: 448235-52-7
N6-[(3R)-1,5-Didehydro-3-methyl-d-prolyl]-l-lysine; l-pyrrolysine.
C12H21N3O3; mol wt 255.31.
C 56.45%, H 8.29%, N 16.46%, O 18.80%.

Description and references

Naturally occurring, genetically encoded amino acid found in certain methanogenic Archaea; originally described as l-lysine ε-amide linked to (4R,5R)-4-substituted-1-pyrroline-5-carboxylate. Identification of pyrrolysine-specific tRNA in Methanosarcina barkeri: G. Srinivasan et al., Science 296, 1459 (2002). Identification as UAG-encoded residue in monomethylamine methyltransferase: B. Hao et al., ibid. 1462. Identification of C4-substituent as a methyl group, synthesis and properties: idem et al., Chem. Biol. 11, 1317 (2004). MS analysis: J. A. Soares et al., J. Biol. Chem. 280, 36962 (2005). Reviews: C. Fenske et al., Angew. Chem. Int. Ed. 42, 606-610 (2003); J. A. Krzycki, Curr. Opin. Microbiol. 8, 706-712 (2005).

Chemical structure

Derivative

Lithium salt.
C12H20LiN3O3; mol wt 261.25.
C 55.17%, H 7.72%, Li 2.66%, N 16.08%, O 18.37%.

Properties

White solid. [α]D20 -2.1° (c = 0.25 in CH3OH). uv max (methanol): 310 nm (sh) (ε 35.4).