Alliinase: Difference between revisions

{{Short description|Class of enzyme}}

| Name = alliin lyase

| EC_number = 4.4.1.4

| GO_codeimage = 0047654 =

| imagewidth =

| widthcaption =

Hence, this enzyme has one [[substrate (biochemistry)|substrate]], ''S''-alkyl-<small>L</small>-[[cysteine]] [[sulfoxide|''S''-oxide]], and two [[product (chemistry)|products]], alkyl [[sulfenic acid|sulfenate]] and 2-amino[[acrylic acid|acrylate2-aminoacrylate]].

This enzyme belongs to the family of [[lyase]]s, specifically the class of carbon-sulfur lyases. The [[List of enzymes|systematic name]] of this enzyme class is '''''S''-alkyl-<small>L</small>-cysteine ''S''-oxide alkyl-sulfenate-lyase (2-aminoacrylate-forming)'''. Other names in common use include '''alliinase''', '''cysteine sulfoxide lyase''', '''alkylcysteine sulfoxide lyase''', '''''S''-alkylcysteine sulfoxide lyase''', '''<small>L</small>-cysteine sulfoxide lyase''', '''''S''-alkyl-<small>L</small>-cysteine sulfoxide lyase''', and '''alliin alkyl-sulfenate-lyase'''. It employs one [[cofactor (biochemistry)|cofactor]], [[pyridoxal phosphate]].

Many alliinases contain a novel ''N''-terminal epidermal growth factor-like domain ([[EGF-like domain]]).<ref name="pmid12235163">{{cite journal | authorvauthors = Kuettner EB, Hilgenfeld R, Weiss MS | title = The active principle of garlic at atomic resolution | journal = J. Biol. Chem. | volume = 277 | issue = 48 | pages = 46402–7 |date=November 2002 | pmid = 12235163 | doi = 10.1074/jbc.M208669200 | urldoi-access = free }}</ref>

[[Image:Cysteine-to-allicin-2D-skeletal.pngsvg|center|500px|Reaction scheme for the conversion: cysteine → alliin → allicin]]

Alliin and related substrates found in nature are [[Chirality (chemistry)|chiral]] at the [[sulfoxide]] position (usually having the ''S'' [[Chirality (chemistry)#By configuration: R- and S-|absolute configuration]], and alliin itself was the first natural product found to have both carbon- and sulfur-centered stereochemistry.<ref name="isbn0-85404-190-7">{{cite book | author = Block, Eric | authorlink = | editor = | others = | title = Garlic and Other Alliums: The Lore and the Science | edition = | language = | publisher = Royal Society of Chemistry | location = Cambridge, Eng | year = 2009 | origyear = | pages = 100–106 | quote = | isbn = 978-0-85404-190-7 | oclc = | doi = | url = | accessdate =9 }}</ref> However, the sulfenic acid intermediate is not chiral, and the final product's stereochemistry is not controlled.

There are a range of similar enzymes that can react with the cysteine-derived sulfoxides present in different species. In onions, an isomer of alliin, isoalliin, is converted to 1-propenesulfenic acid. A separate enzyme, the lachrymatory factor synthase or LFS, then converts this chemical to [[syn-propanethial-S-oxide|''syn''-propanethial-''S''-oxide]], a potent [[lachrymator]]. The analogous [[butyl]] compound, ''syn''-butanethial-''S''-oxide, is found in ''[[Allium siculum]]'' species.<ref>{{cite journal |authorvauthors =Kubec R, Cody RB, Dane AJ, Musah RA, Schraml J, Vattekkatte A, Block E|year=2010|month= |title=Applications of Direct Analysis in Real Time−Mass Spectrometry (DART-MS) in ''Allium'' Chemistry. (''Z'')-Butanethial ''S''-Oxide and 1-Butenyl Thiosulfinates and their ''S''-(''E'')-1-Butenylcysteine ''S''-Oxide Precursor from ''Allium siculum''|journal= Journal of Agricultural and Food Chemistry|volume= 58 |pmid=20047275|issue= 2|pages= 1121–1128|id= |doi=10.1021/jf903733e}}</ref>

* {{cite journal | authorvauthors = Durbin RD and, Uchytil TF | year = 1971 | title = Purification and properties of alliin lyase from the fungus ''Penicillium corymbiferum'' | journal = Biochim.Biochimica Biophys.et Biophysica Acta —(BBA) - Enzymology | volume = 235 |issue= 3 |pages = 518–520 |doi= 10.1016/0005-2744(71)90293-2 }}

* {{cite journal | last = Goryachenkova | first=E. V. | year = 1952 | trans_title trans-title= Enzyme in garlic which forms allycine (allyinase), a protein with phosphopyridoxal | language=Russianru | journal = [[Doklady Akademii Nauk SSSR]] | volume = 87 | pages = 457–460 |title=Фермент в чесноке, который формирует allycine (allyinase), белок с phosphopyridoxal}}

* {{cite journal | authorvauthors = Jacobsen JV, Yamaguchi M, Howard FD and, Bernhard RA | year = 1968 | title = Product inhibition of the cysteine sulfoxide lyase of ''tulbaghia violacea'' | journal = Arch. Biochem. Biophys. | volume = 127 | pages = 252–258 | doi = 10.1016/0003-9861(68)90223-3 }}

* [https://web.archive.org/web/20090720113506/http://www.biologie.uni-hamburg.de/lehre/bza/taste/1lk9/1lk9text.htm Genuine Garlic:Alliinase from ''Allium sativum''.]

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