Phenol sulfatase

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Pregnancy urine has been found to be a rich source of estrogens and related compounds. They are generally excreted as sulfates or glucu-ronosides, and are liberated from the esters by acid hydrolysis, phenol-sulfatase, and j8-glucuronidase. The 18-carbon steroids isolated from mammalian urine show close similarity (Table VIII and Fig. 18). They... 

Sample incubated with glucuronidase and sulfatase at pFl 5 and 37 C, FIjSCh added and steam distilled (total phenol) and analyzed FlPLC-electrochemical detector 2 ng/ injection 95-107% Schaltenbrand and Coburn 1985... 

A number of enzymes known as sulfuric ester hydrolases (EC 3.1.6) are able to hydrolyze sulfuric acid esters. They comprise arylsulfatase (sulfatase, EC 3.1.6.1), steryl-sulfatase (steroid sulfatase, steryl-sulfate sulfohydrolase, arylsulfatase C, EC 3.1.6.2), choline-sulfatase (choline-sulfate sulfohydrolase, EC 3.1.6.6), and monomethyl-sulfatase (EC 3.1.6.16). Whereas mono-methyl-sulfatase is highly specific and does not act on higher homologues, arylsulfatase has a broad substrate specificity and is of particular significance in the hydrolysis of sulfate conjugates of phenols, be they endogenous compounds, drugs, or their metabolites [167-169],... 

Arylsulfatase [EC 3.1.6.1 ], also known simply as sulfatase, catalyzes the hydrolysis of a phenol sulfate, thereby producing a phenol and sulfate. This enzyme classification represents a collection of enzymes with rather similar specificities. (1) Steryl-sulfatase [EC3.1.6.2],also referred to as arylsulfatase C and steroid sulfatase, catalyzes the hydrolysis of 3-j8-hydroxyandrost-5-en-17-one 3-sulfate to 3-j8-hydroxyandrost-5-en-17-one and sulfate. The enzyme utilizes other steryl sulfates as substrates. (2) Cere-broside-sulfatase [EC 3.1.6.8], or arylsulfatase A, catalyzes the hydrolysis of a cerebroside 3-sulfate to yield a cerebroside and sulfate. The enzyme will also hydrolyze the galactose 3-sulfate bond present in a number of lipids. In addition, the enzyme will also hydrolyze ascorbate 2-sulfate and other phenol sulfates. 

Urines (10 cm ) are first hydrolyzed with sulfatase-glucuron-idase preparations prior to extraction and assay of phenolic alcohols. 

Taylor and coworkers have prepared o-fluoromethyl and o-difluoromethyl estrone sulfates82 and shown that these compounds are good substrates for steroid sulfatases.83 The phenol product of hydrolysis of o-fluoromethyl estrone sulfate undergoes heterolytic cleavage to form a quinone methide that inactivates the steroid sulfatase (Scheme 20C).83 The phenol product of hydrolysis of o-difluoromethyl estrone sulfate breaks down first to a quinone methide and then to the o-formyl estrone, which also inactivates the steroid sulfatase.83... 

Balance between the active and inactive forms of ecdysone and/or other ecdysteroids may be accomplished by the formation of conjugates such as sulfate esters or glucosides (20,27). The sulfation of phenols and a variety of sterols has been 3emonstrated in insect tissues and this, in close association with an appropriate sulfatase, would constitute a readily reversible mechanism whereby the required balance between active and inactive forms of ecdysteroids could be regulated (27). 

The pK a and therefore the physicochemical properties of a series of aminosulfonate-based compounds of phenol is correlated with the irreversible inhibition of the enzyme estrone sulfatase (ES). A strong correlation exists between the observed pK a and inhibitory activity. The stability of the phenoxide ion, as indicated by the acid dissociation constant, is an important factor in the irreversible inhibition of this enzyme. 

Inert metal ion aqua complexes such as [Cr(NH3)5(OH2)] can accelerate the hydrolysis of phosphate esters. These species are believed to act as a general base catalyst. On the other hand, CrOj inhibits the enzyme action of phosphatase and sulfatase and the inhibitary action is enhanced by the addition of phenol. Certain Cr(III) complexes can also act as catalysts in the electrocatalytic reduction of CO2 to MeOH, but they are not as efficient as iron complexes. 

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