Desmosine

Desmosine is an amino acid found uniquely in elastin, a protein found in connective tissue such as skin, lungs, and elastic arteries.

Desmosine
Names
IUPAC name
6-{4-[(4S)-4-Amino-4-carboxybutyl]-3,5-bis[(3S)-3-amino-3-carboxypropyl]-1-pyridiniumyl}-L-norleucine
Identifiers
3D model (JSmol)
4074277
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C24H39N5O8/c25-17(21(30)31)5-1-2-11-29-12-14(7-9-19(27)23(34)35)16(4-3-6-18(26)22(32)33)15(13-29)8-10-20(28)24(36)37/h12-13,17-20H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37)/p+1 Y
    Key: VEVRNHHLCPGNDU-MUGJNUQGSA-O Y
SMILES
  • O=C(O)[C@@H](N)CCCC[n+]1cc(c(c(c1)CC[C@@H](C(=O)O)N)CCC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N
Properties
C24H40N5O8
Molar mass 526.611 g·mol−1
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

Desmosine is a component of elastin and cross links with its isomer, isodesmosine, giving elasticity to the tissue. Detection of desmosine in urine, plasma or sputum samples can be a marker for elastin breakdown due to high elastase activity related to certain diseases.

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