Hypusine

Hypusine

Names
IUPAC name 2-Amino-6-[(4-amino-2-hydroxybutyl)amino]hexanoic acid[1]
Other names N6-(4-Amino-2-hydroxybutyl)lysine
Identifiers
CAS Number	34994-11-1 (2S)-2-Amino, -6-{[(2R)-2-hydroxybutyl]amino} Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:21858 N
ChemSpider	10624726 N 16740599 (2S)-2-Amino N 9097677 (2S)-2-Amino, -6-{[(2R)-2-hydroxybutyl]amino} N 58862 (2S)-2-Amino, -6-{[(2S)-2-hydroxybutyl]amino} N
MeSH	hypusine
PubChem	21878228 15930878 (2S)-2-Amino 10922432 (2S)-2-Amino, -6-{[(2R)-2-hydroxybutyl]amino} 65396 (2S)-2-Amino, -6-{[(2S)-2-hydroxybutyl]amino}
InChI InChI=1S/C10H23N3O3/c11-5-4-8(14)7-13-6-2-1-3-9(12)10(15)16/h8-9,13-14H,1-7,11-12H2,(H,15,16) N Key: BZUIJMCJNWUGKQ-UHFFFAOYSA-N N
SMILES NCCC(O)CNCCCCC(N)c(:[o]):[oH] NCCC(O)CNCCCCC(N)C(O)=O
Properties
Chemical formula	C10H23N3O3
Molar mass	233.31 g·mol−1
Related compounds
Related alkanoic acids	4-(γ-Glutamylamino)butanoic acid Saccharopine
Related compounds	Palmitoylethanolamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Hypusine is an unusual amino acid found in all eukaryotes and in some archaea, but not in bacteria. The only known protein containing hypusine is eukaryotic translation initiation factor 5A (eIF5A) and a similar protein found in archaebacteria.^[2] In humans, two isoforms of eIF-5A have been described: eIF5A-1 and eIF5A-2. They are encoded by two different genes EIF5A and EIF5A2. The protein is involved in protein biosynthesis and promotes the formation of the first peptide bond. The region surrounding the hypusine residue is highly conserved and is essential to the function of eIF5A.^[3] Thus, hypusine and eIF-5A appear to be vital for the viability and proliferation of eukaryotic cells.

Hypusine is formed in eIF-5A by post-translational modification of one of the lysyl residues. There are two reactions and two enzymes involved:

• 1. Deoxyhypusine synthase catalyzes the cleavage of the polyamine spermidine and transfer of its 4-aminobutyl moiety to the ε-amino group of one specific lysine residue of the eIF-5A precursor to form deoxyhypusine and 1,3-diaminopropane.
• 2. Deoxyhypusine hydroxylase mediates the formation of hypusine by addition of a hydroxyl group to the deoxyhypusine residue.

An excess of hypusine was found in the urine of children and patients with familial hyperlysinemia.

Hypusine was first isolated from bovine brain by Japanese scientists Shiba et al. in 1971.^[4] The name hypusine indicates that the molecule comprises moieties of hydroxyputrescine and lysine.

References