Desmosine

Desmosine

Names
IUPAC name 6-{4-[(4S)-4-Amino-4-carboxybutyl]-3,5-bis[(3S)-3-amino-3-carboxypropyl]-1-pyridiniumyl}-L-norleucine
Identifiers
CAS Number	11003-57-9
3D model (Jmol)	Interactive image
ChemSpider	13085543
PubChem	25435
UNII	4MOL2J0TLY
InChI 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 Key: VEVRNHHLCPGNDU-MUGJNUQGSA-O
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
Chemical formula	C24H40N5O8
Molar mass	526.61 g·mol^−1
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

A desmosine cross-link is formed from three allysyl side chains plus one unaltered lysyl side chain from the same or neighbouring polypeptides. 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.^[1][2]

It is found in elastin. Desmosine causes a yellow color.

This desmosine is responsible for the rubber properties of elastin.

References

1. Millipore product catalogue, purified desmosine http://www.millipore.com/catalogue/item/263275-5mg
2. Ma, S; Turino, G. M.; Lin, Y. Y. (2011). "Quantitation of desmosine and isodesmosine in urine, plasma, and sputum by LC-MS/MS as biomarkers for elastin degradation". Journal of Chromatography B. 879 (21): 1893–8. doi:10.1016/j.jchromb.2011.05.011. PMID 21621489.