Allysine

{{distinguish|Allicin}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477318310

| ImageFile=Allysine.svg

| ImageAlt = Skeletal formula of zwitterion

| ImageFile1 = L-Allysine-zwitterion-3D-balls.png

| ImageAlt1 = Ball-and-stick model of the L-allysine molecule as a zwitteiron

| PIN = (2S)-2-Amino-6-oxohexanoic acid

| OtherNames=2-aminoadipate semialdehyde, 2-amino-5-formylvaleric acid, norvaline, 6-oxo-DL-norleucine

|Section1={{Chembox Identifiers

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C04076

| InChI = 1/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)/t5-/m0/s1

| InChIKey = GFXYTQPNNXGICT-YFKPBYRVBJ

| InChI1 = 1/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)

| InChIKey1 = GFXYTQPNNXGICT-UHFFFAOYAD

| SMILES1 = O=CCCCC(N)C(=O)O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GFXYTQPNNXGICT-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=1962-83-0

| CASNo_Comment =

| CASNo1 = 6665-12-9

| CASNo1_Comment = L-enantiomer

| PubChem=207

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 202

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 425I4Y24YZ

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 57988

| SMILES = O=CCCC[C@H](N)C(=O)O

| MeSHName=allysine

}}

|Section2={{Chembox Properties

| C=6 | H=11 | N=1 | O=3

| Appearance= unstable

| Density=1.74g/cm³

| MeltingPt=

| BoilingPtC=295.2

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPtC = 132.3

| AutoignitionPtC =

}}

}}

Allysine is a derivative of lysine that features a formyl group in place of the terminal amine. The free amino acid does not exist, but the allysine residue does. It is produced by aerobic oxidation of lysine residues by the enzyme lysyl oxidase. The transformation is an example of a post-translational modification. The semialdehyde form exists in equilibrium with a cyclic derivative.{{cite journal |doi=10.1007/s00726-003-0012-1 |title=Recent Advances in the Analysis of Oxidized Proteins |year=2003 |last1=Requena |first1=J. R. |last2=Levine |first2=R. L. |last3=Stadtman |first3=E. R. |journal=Amino Acids |volume=25 |issue=3–4 |pages=221–226 |pmid=14661085 |s2cid=28837698 }}

File:PTMofLysine.svg

Allysine is involved in the production of elastin and collagen.{{cite journal | doi = 10.1146/annurev.bi.53.070184.003441| title = Cross-Linking in Collagen and Elastin| year = 1984| last1 = Eyre| first1 = David R.| last2 = Paz| first2 = Mercedes A.| last3 = Gallop| first3 = Paul M.| journal = Annual Review of Biochemistry| volume = 53| pages = 717–748| pmid = 6148038}} Increased allysine concentration in tissues has been correlated to the presence of fibrosis.{{cite journal | vauthors = Wahsner J, Désogère P, Abston E, Graham-O'Regan KA, Wang J, Rotile NJ, Schirmer MD, Santos Ferreira DD, Sui J, Fuchs BC, Lanuti M, Caravan P | display-authors = 6 | title = ⁶⁸Ga-NODAGA-Indole: An Allysine-Reactive Positron Emission Tomography Probe for Molecular Imaging of Pulmonary Fibrogenesis | journal = Journal of the American Chemical Society | volume = 141 | issue = 14 | pages = 5593–5596 | date = April 2019 | pmid = 30908032 | pmc = 6494104 | doi = 10.1021/jacs.8b12342 }}

Allysine residues react with sodium 2-naphthol-6-sulfonate to produce a fluorescent bis-naphtol-allysine product.{{cite journal | vauthors = Waghorn PA, Oliveira BL, Jones CM, Tager AM, Caravan P | title = High sensitivity HPLC method for determination of the allysine concentration in tissue by use of a naphthol derivative | journal = Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences | volume = 1064 | pages = 7–13 | date = October 2017 | pmid = 28886479 | pmc = 5662445 | doi = 10.1016/j.jchromb.2017.08.032 }} In another assay, allysine-containing proteins are reduced with sodium borohydride to give a peptide containing the 6-hydroxynorleucine (6-hydroxy-2-aminocaproic acid) residue, which (unlike allysine) is stable to proteolysis.