Cyclisation with Multiple S-S Bonds

Cyclisation with Multiple S-S Bonds

Novazym is able to build disulfide bridges regio-specifically between cysteines at specified positions. We are able to introduce up to four customized disulfide bridges on one peptide, by applying either native folding or a variety site-specific orthogonal chemistries.

Description

When peptides contain multiple cysteine residues, challenges arise due to the random formation of disulfide bridges between them. Novazym is able to build disulfide bridges regio-specifically between cysteines at specified positions. We are able to introduce up to four customized disulfide bridges on one peptide, by applying either native folding or a variety site-specific orthogonal chemistries.

A common method for this kind of reactions is native folding. This thermodynamic stability strategy requires to precisely mimic the ideal conditions required for the species to fold, which are very specific for each peptide. However, in several cases isomers may appear in the reaction mixture, which are difficult to remove with prep-HPLC and results in poor yields. Therefore we have developed various methods to couple cysteine-pairs regio-selectively at specified positions. We are capable to introduce up to four customized disulfide bridges on one peptide, via site-specific orthogonal chemistry.

Using a defined combination of cysteine protecting groups we are able to de-protect and oxidize the cysteine couples individually. This leads not only to regio-specific disulfide bridge formation, but also relative high yield and purity compared with traditional methods.

Cys-Cys Cyclization
Peptide NamePeptide SequenceDisulfide bonds
alpha Defensin 1 (human)ACYCRIPACIAGERRYGTCIYQGRLWAFCCC2-C30, C4-C19, C9-C29
alpha Defensin 2 (human)CYCRIPACIAGERRYGTCIYQGRLWAFCCC1-C29, C3-C18, C8-C28
alpha Defensin 3 (human)DCYCRIPACIAGERRYGTCIYQGRLWAFCCC2-C30, C4-C19, C9-C29
alpha Defensin 4 (human)VCSCRLVFCRRTELRVGNCLIGGVSFTYCCTRVC2-C30, C4-C19, C9-C29
alpha Defensin 5 (human)ATCYCRTGRCATRESLSGVCEISGRLYRLCCRC3-C31, C5-C20, C10-C30
alpha Defensin 6 (human)AFTCHCRRSCYSTEYSYGTCTVMGINHRFCCLC4-C31, C6-C20, C10-C30
beta Defensin 1 (human)DHYNCVSSGGQCLYSACPIFTKIQGTCYRGKAKCCKC5-C34, C12-C27, C17-C35
beta Defensin 2 (human)GIGDPVTCLKSGAICHPVFCPRRYKQIGTCpEGTKCCKKPC8-C37, C15-C30, C20-C38
beta Defensin 3 (human)GIINTLQKYYCRVRGGRCAVLSCLPKEEQIGKCSTRGRKCCRRKKC11-C40, C18-C33, C23-C41
beta Defensin 4 (human)ELDRICGYGTARCRKKCRSQEYRIGRCPNTYACCLRKC6-C33, C13-C27, C17-C34

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