Catalytic triad of serine proteases

Protein engineering (continued) differential and uniform binding energy changes 438,439 dissection of catalytic triad of serine proteases 450-452 domain structure analysis... 

Frey, P., Whitt, S., and Tobin, J. (1994) A low barrier hydrogen bond in the catalytic triad of serin protease,... 

The second group of approaches, seeking similarities in the shapes and chemical surface properties of binding sites, include recently developed tools such as CavBase [89, 90], eF-Site [91], and SuMo [92]. An earlier technique using surface shape only for binding site comparisons was reported by Rosen et al. [93], The reliability of this geometric surface-matching approach has been shown for the catalytic triad of serine proteases and chorismate mutase. 

Mechanistic and structural investigations have revealed that while some esterase antibodies promote direct attack by hydroxide on the ester function [ 15], others unexpectedly may also use a covalent mechanism involving a serine-histidine dyad strongly reminiscent of the catalytic triad of serine proteases [16]. 

Frey, P. A., Whitt, S. A., Tobin, J. B., A Low-Barrier Hydrogen Bond in the Catalytic Triad of Serine Proteases, Science 1994, 264, 1927-1930. 

J.B. Tobin, S.A. Whitt, C.S. Cassidy and P.A. Frey, Low-barrier hydrogen bonding in molecular complexes analogous to histidine and aspartate in the catalytic triad of serine proteases, Biochem., 34 (1995) 6919. 

Ester hydrolysis, esterification or acylation, and transesterification reactions play an important role in nature and organic synthesis including the synthesis of natural products [1, 2], Applications of hydrolytic or esterification reactions range from laboratory syntheses (e.g. with the acyl moiety as key intermediate or as protecting group) to industrial scale production of bulk chemicals, biodiesel or food (e.g. ester units as building blocks for polymerisation and polycondensation reactions, transesterification of triglycerides) [3, 4]. Transesterification reactions in nature include for example enzymatic reactions of lipases, esterases and other hydrolases that rely on the catalytic triad of serine proteases, which will be discussed in the first part of this section [5-8]. 

Because of the similarity of the catalytic triad of serine proteases and lipases, the same protease inhibitors have been utilized in studies of lipases. Transition state analogues such as butylboronic acid and phenylboronic acid... 

---