Pyrrolysine
Title: Pyrrolysine
CAS Registry Number: 448235-52-7
CAS Name: N6-[(3R)-1,5-Didehydro-3-methyl-D-prolyl]-L-lysine
Additional Names: L-pyrrolysine
Molecular Formula: C12H21N3O3
Molecular Weight: 255.31
Percent Composition: C 56.45%, H 8.29%, N 16.46%, O 18.80%
Literature References: Naturally occurring, genetically encoded amino acid found in certain methanogenic Archaea; originally described as L-lysine e-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).
 
Derivative Type: Lithium salt
Molecular Formula: C12H20LiN3O3
Molecular Weight: 261.25
Percent Composition: C 55.17%, H 7.72%, Li 2.66%, N 16.08%, O 18.37%
Properties: White solid. [a]D20 -2.1° (c = 0.25 in CH3OH). uv max (methanol): 310 nm (sh) (e 35.4).
Optical Rotation: [a]D20 -2.1° (c = 0.25 in CH3OH)
Absorption maximum: uv max (methanol): 310 nm (sh) (e 35.4)

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