Investigation of Serine-Proteinase-Catalyzed Peptide Splicing in Analogues of Sunflower Trypsin Inhibitor 1 (SFTI-1)

Chembiochem. 2015 Sep 21;16(14):2036-45. doi: 10.1002/cbic.201500296. Epub 2015 Aug 17.

Abstract

Serine-proteinase-catalyzed peptide splicing was demonstrated in analogues of the trypsin inhibitor SFTI-1: both single peptides and two-peptide chains (C- and N-terminal peptide chains linked by a disulfide bridge). In the second series, peptide splicing with catalytic amount of proteinase was observed only when formation of acyl-enzyme intermediate was preceded by hydrolysis of the substrate Lys-Ser peptide bond. Here we demonstrate that with an equimolar amount of the proteinase, splicing occurs in all the two-peptide-chain analogues. This conclusion was supported by high resolution crystal structures of selected analogues in complex with trypsin. We showed that the process followed a direct transpeptidation mechanism. Thus, the acyl-enzyme intermediate was formed and was immediately used for a new peptide bond formation; products associated with the hydrolysis of the acyl-enzyme were not observed. The peptide splicing was sequence- not structure-specific.

Keywords: SFTI-1; enzymes; inhibitors; peptide splicing.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Cattle
  • Crystallography, X-Ray
  • Helianthus / chemistry
  • Models, Molecular
  • Molecular Sequence Data
  • Peptides / chemistry
  • Peptides / metabolism*
  • Peptides, Cyclic / chemical synthesis
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / pharmacology*
  • Serine Proteases / chemical synthesis
  • Serine Proteases / chemistry
  • Serine Proteases / pharmacology
  • Trypsin / chemistry
  • Trypsin / metabolism*
  • Trypsin Inhibitors / chemical synthesis
  • Trypsin Inhibitors / chemistry*
  • Trypsin Inhibitors / pharmacology*

Substances

  • Peptides
  • Peptides, Cyclic
  • SFTI-1 peptide, sunflower
  • Trypsin Inhibitors
  • Serine Proteases
  • Trypsin