Title: Hypusine
CAS Registry Number: 34994-11-1
CAS Name: N6-[(2R)-4-Amino-2-hydroxybutyl]-L-lysine
Additional Names: (2S,9R)-2,11-diamino-9-hydroxy-7-azaundecanoic acid; N6-(4-amino-2-hydroxybutyl)-2,6-diaminohexanoic acid
Molecular Formula: C10H23N3O3
Molecular Weight: 233.31
Percent Composition: C 51.48%, H 9.94%, N 18.01%, O 20.57%
Literature References: Naturally occurring L-amino acid formed by the post-translational modification of lysine. Name coined to indicate the condensation product of hydroxyputrescine with lysine. Isoln: T. Shiba et al., Biochim. Biophys. Acta 244, 523 (1971); from archaebacteria: H. Schümann, F. Klink, Syst. Appl. Microbiol. 11, 103 (1989). In eukaryotes occurs only at a single position in one protein, eukaryotic protein synthesis initiation factor 5A, (eIF-5A, formerly eIF-4D): M. H. Park et al., Proc. Natl. Acad. Sci. USA 78, 2869 (1981); H. L. Cooper et al., ibid. 80, 1854 (1983). Biosynthesis: M. H. Park et al., J. Biol. Chem. 257, 7217 (1982); M. H. Park et al., ibid. 259, 12123 (1984). Synthesis and stereochemistry: T. Shiba et al., Bull. Chem. Soc. Jpn. 55, 899 (1982). Total synthesis: C. M. Tice, B. Ganem, J. Org. Chem. 48, 5043, 5048 (1983); R. J. Bergeron et al., ibid. 58, 6804 (1993). Biological significance in eukaryotes: J. W. B. Hershey et al., Biochim. Biophys. Acta 1050, 160 (1990). HPLC determn in eukaryotic samples: S. Beninati et al., Anal. Biochem. 184, 16 (1990). Chromatographic determn in archaebacteria: D. Bartig, F. Klink, J. Chromatogr. 606, 43 (1992). Review of biological significance: M. H. Park et al., Trends Biochem. Sci. 18, 475-479 (1993).
Derivative Type: Dihydrochloride
CAS Registry Number: 82310-93-8
Molecular Formula: C10H23N3O3.2HCl
Molecular Weight: 306.23
Percent Composition: C 39.22%, H 8.23%, N 13.72%, O 15.67%, Cl 23.15%
Properties: White crystals, mp 239-241° (dec). [a]D23 +8.3° (c = 0.96 in 6M HCl).
Melting point: mp 239-241° (dec)
Optical Rotation: [a]D23 +8.3° (c = 0.96 in 6M HCl)
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