MetaCyc Enzyme: sulfenic acid dehydrogenase

Synonyms: sulfenate dehydrogenase, lachrymatory-factor synthase

Species: Petiveria alliacea

Subunit composition of sulfenic acid dehydrogenase = [lachrymatory-factor synthase α subunit]2[lachrymatory-factor synthase γ subunit][lachrymatory-factor synthase δ subunit]

The Amazonian medicinal plant Petiveria alliacea contains a unique sulfine lachrymator, (Z)-phenylmethanethial S-oxide, which is produced by a unique lachrymatory-factor synthase. The enzyme acts on phenylmethanesulfenate, which is produced by the (Z)-phenylmethanethial S-oxide alliinase from petiveriin [Musah09].

The lachrymatory-factor synthase was isolated from root tissue of Petiveria alliacea, and chromatographically purified and characterized by SDS-PAGE [Musah09].

Unlike the enzyme from onion, which was reported to contain only one type of subunit (of 19kDa), the enzyme from Petiveria alliacea is a heterotetrameric glycoprotein comprised of two α-subunits (68.8 kD each), one γ-subunit (22.5 kD), and one δ-subunit (11.9 kD). The α subunits are glycosylated and linked together by a disulfide bridge [Musah09]. In addition, while the enzyme from onion is an isomerase that catalyzes the rearrangement of (E) 1-propenylsulfenate to (Z)-propanethial S-oxide, the enzyme from Petiveria alliacea is a dehydrogenase. Enzymatic activity was enhanced in the presence of NAD+ or NADP+, but not in the presnce of FAD of FMN | [He11].

In the absence of the enzyme, phenylmethanesulfenate dimerizes spontaneouly and forms petivericin [Musah09].

Molecular Weight: 172.0 kD (experimental) [Musah09 ]

pI: 5.2 [Musah09]

Gene-Reaction Schematic: ?

Gene-Reaction Schematic

Created 01-Jul-2010 by Pujar A , Boyce Thompson Institute
Revised 04-Dec-2014 by Caspi R , SRI International

Enzymatic reaction of: phenylmethanesulfenate dehydrogenase (sulfenic acid dehydrogenase)

Synonyms: (Z)-phenylmethanethial S-oxide synthase

EC Number: 1.1.1.M1

phenylmethanesulfenate + NAD(P)+ <=> (Z)-phenylmethanethial S-oxide + NAD(P)H + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

The reaction is favored in the direction shown.

In Pathways: (Z)-phenylmethanethial S-oxide biosynthesis

Subunit of sulfenic acid dehydrogenase: lachrymatory-factor synthase α subunit

Molecular Weight: 68.8 kD (experimental) [Musah09]

Subunit of sulfenic acid dehydrogenase: lachrymatory-factor synthase γ subunit

Molecular Weight: 22.5 kD (experimental) [Musah09]

Subunit of sulfenic acid dehydrogenase: lachrymatory-factor synthase δ subunit

Molecular Weight: 11.9 kD (experimental) [Musah09]


He11: He Q, Kubec R, Jadhav AP, Musah RA (2011). "First insights into the mode of action of a "lachrymatory factor synthase" - Implications for the mechanism of lachrymator formation in Petiveria alliacea, Allium cepa and Nectaroscordum species." Phytochemistry 72(16);1939-46. PMID: 21840558

Musah09: Musah RA, He Q, Kubec R (2009). "Discovery and characterization of a novel lachrymatory factor synthase in Petiveria alliacea and its influence on alliinase-mediated formation of biologically active organosulfur compounds." Plant Physiol 151(3);1294-303. PMID: 19692535

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Mon Aug 3, 2015, BIOCYC13B.