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^Y
3D model (Jmol)	Interactive image
ChemSpider	13085543^N
PubChem	25435
UNII	4MOL2J0TLY^N
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^Y Key: VEVRNHHLCPGNDU-MUGJNUQGSA-O^N
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).
N verify (what is ^YN ?)
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

↑ Millipore product catalogue, purified desmosine http://www.millipore.com/catalogue/item/263275-5mg
↑ 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.

Protein primary structure and posttranslational modifications

General

N terminus

C terminus

Single specific AAs

Serine/Threonine	Phosphorylation Dephosphorylation Glycosylation Methylidene-imidazolone (MIO) formation

Tyrosine	Phosphorylation Dephosphorylation Sulfation Porphyrin ring linkage Adenylylation Flavin linkage Topaquinone (TPQ) formation Detyrosination

Cysteine	Palmitoylation Prenylation

Aspartate	Succinimide formation

Glutamate	Carboxylation Methylation Polyglutamylation Polyglycylation

Asparagine	Deamidation Glycosylation

Glutamine	Transglutamination

Lysine	Methylation Acetylation Acylation Adenylylation Hydroxylation Ubiquitination Sumoylation ADP-ribosylation Deamination Oxidative deamination to aldehyde O-glycosylation Imine formation Glycation Carbamylation Succinylation

Arginine	Citrullination Methylation ADP-ribosylation

Proline	Hydroxylation

Histidine	Diphthamide formation Adenylylation

Tryptophan	C-mannosylation

Crosslinks between two AAs

Cysteine-Cysteine	Disulfide bond

Methionine-Hydroxylysine	Sulfilimine bond

Lysine-Tyrosylquinone	Lysine tyrosylquinone (LTQ) formation

Tryptophan-Tryptophylquinone	Tryptophan tryptophylquinone (TTQ) formation

Three consecutive AAs
(chromophore formation)

Serine–Tyrosine–Glycine	p-Hydroxybenzylidene-imidazolinone formation

Histidine–Tyrosine–Glycine	4-(p-hydroxybenzylidene)-5-imidazolinone formation

Crosslinks between four AAs

Allysine-Allysine-Allysine-Lysine	Desmosine

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