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Lysidine (nucleoside)

Lysidine is an uncommon nucleoside, rarely seen outside of tRNA. It is a derivative of cytidine in which the carbonyl is replaced by the amino acid lysine. The first position, i.e. the wobble base, in the anti-codon of the eubacterial isoleucine-specific tRNA pertaining to the AUA codon is typically changed from a cytidine which would pair with guanosine to a lysidine which will base pair with adenosine. Lysidine improves translation fidelity because uridine cannot be used at this position even though it is a conventional partner for adenosine since it will also "wobble base pair" with guanosine. Lysidine is denoted as L or k2C (lysine bound to C2 atom of cytidine).

Hydrogen bonding (arrows) in the lysidine ('''L''') and adenosine ('''A''') base pair, compared against the cytidine ('''C''') and guanosine ('''G''') base pair.

References

(24 May 2005). "Structural basis for lysidine formation by ATP pyrophosphatase accompanied by a lysine-specific loop and a tRNA-recognition domain". Proceedings of the National Academy of Sciences of the United States of America.
(April 2009). "The Catalytic Flexibility of tRNAIle-lysidine Synthetase Can Generate Alternative tRNA Substrates for Isoleucyl-tRNA Synthetase". Journal of Biological Chemistry.
(October 2009). "Structural basis for translational fidelity ensured by transfer RNA lysidine synthetase". Nature.
(19 September 2008). "Conformational Preferences of Hypermodified Nucleoside Lysidine (k²C) Occurring at 'Wobble' Position in Anticodon Loop of tRNA^Ile". Nucleosides, Nucleotides & Nucleic Acids.

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nucleosides pyrimidines hydroxymethyl-compounds amidines

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