Lysidine (nucleoside)

Lysidine (nucleoside)
Names
	IUPAC name 2-Amino-6-[4-amino-1-(3,4-dihydroxy-5-hydroxymethyloxolan-2-yl)-1H-pyrimidin-2-ylideneamino]hexanoic acid
	Other names 4-Amino-2-(N(6)-lysino)-1-ribofuranosylpyrimidine
Identifiers
CAS Number	144796-96-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	24604124 ;
PubChem CID	44124149;
	InChI InChI=1S/C15H25N5O6/c16-8(14(24)25)3-1-2-5-18-15-19-10(17)4-6-20(15)13-12(23)11(22)9(7-21)26-13/h4,6,8-9,11-13,21-23H,1-3,5,7,16H2,(H,24,25)(H2,17,18,19)/t8-,9+,11+,12+,13+/m0/s1 Key: MDWUIKMWKDMPDE-IINAIABHSA-N;
	SMILES OC[C@H]1O[C@@H](N2C=CC(N)=N/C2=N\CCCC[C@H](N)C(O)=O)[C@H](O)[C@@H]1O;
Properties
Chemical formula	C15H25N5O6
Molar mass	371.39 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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 third position in the anti-codon of the Isoleucine-specific tRNA, is typically changed from a cytidine which would pair with guanosine to a lysidine which will base pair with adenosine. Uridine could not be used at this position even though it is a conventional partner for adenosine since it will also "wobble base pair" with guanosine. So lysidine allows better translation fidelity.^[1]^[2]

Lysidine base pairs with Adenosine in context of a Cytidine to Guanosine base pair. R = ribose. Arrows indicate hydrogen bonds going from hydrogens to bond acceptor. The notation for lysidine, L, is depicted above.

References

↑ Nakanishi K, Fukai S, Ikeuchi Y, et al. (May 2005). "Structural basis for lysidine formation by ATP pyrophosphatase accompanied by a lysine-specific loop and a tRNA-recognition domain". Proc. Natl. Acad. Sci. U.S.A. 102 (21): 7487–7492. doi:10.1073/pnas.0501003102. PMC 1140429. PMID 15894617.
↑ Salowe SP, Wiltsie J, Hawkins JC, Sonatore LM (Apr 10, 2009). "The Catalytic Flexibility of tRNAIle-lysidine Synthetase Can Generate Alternative tRNA Substrates for Isoleucyl-tRNA Synthetase". J Biol Chem. 284 (15): 9656–9662. doi:10.1074/jbc.M809013200. PMC 2665086. PMID 19233850.

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[1] Nakanishi K, Fukai S, Ikeuchi Y, et al. (May 2005). "Structural basis for lysidine formation by ATP pyrophosphatase accompanied by a lysine-specific loop and a tRNA-recognition domain". Proc. Natl. Acad. Sci. U.S.A. 102 (21): 7487–7492. doi:10.1073/pnas.0501003102. PMC 1140429. PMID 15894617.

[2] Salowe SP, Wiltsie J, Hawkins JC, Sonatore LM (Apr 10, 2009). "The Catalytic Flexibility of tRNAIle-lysidine Synthetase Can Generate Alternative tRNA Substrates for Isoleucyl-tRNA Synthetase". J Biol Chem. 284 (15): 9656–9662. doi:10.1074/jbc.M809013200. PMC 2665086. PMID 19233850.