Abstract:Two PEG-based polymer supported methionine selenoxide (MeSeO) named TentaGel-MetSeO and PEG-MetSeO were synthesized and used as immobilized oxidants for the purpose of formation of disulfide bonds in peptides under aqueous conditions. Peptide disulfide bonds were successfully synthesized by use of the two immobilized oxidants. Moreover, the oxidation of the methionine residue to its sulfoxide derivate was not observed. By comparison, the yield of disulfidecontaining peptide via PEG-MetSeO oxidation is higher t… Show more
“…Regioselectvie synthesis of two disulfide bonds by the use of the BSA-ODr approach Recently, methionine selenoxide (MetSeO) as an oxidation and deprotecting reagent was used to construct two disulfide bonds in peptides (named SeODR) in a one-pot manner in our laboratories. 18 Inspired by the SeODR reaction, we considered that BSA may also be used to regioselectively construct two disulfide bonds in peptides. Thus, the synthesis of two disulfide bonds in α-conotoxin SI was first investigated by reaction of linear α-conotoxin SI-1 with BSA.…”
Section: Resultsmentioning
confidence: 99%
“…It was reported that Br − was a facilitator of the SeODR approach. 18 Thus, the reaction of BSA with oxy (Acm) was also investigated in HBr solution. As expected, oxytocin was successfully generated (entries v-viii).…”
“…4 and S40 †). 18 Next, the synthesis of three disulfide bonds in conotoxin mr3e by the use of the BSA oxidation method was investigated in phosphate buffer. The results are shown in Table S5 † and Fig.…”
Section: Synthesis Of Mbds By the Bsa Oxidation Reactionmentioning
confidence: 99%
“…Fig.5HPLC chromatograms: (a) reduced conotoxin mr3e, (b) reduced conotoxin mr3e was aged for 3 h in pH 7.0 phosphate buffer solution, (c) reduced conotoxin mr3e reacted with BSA for 45 min in pH 7.0 phosphate buffer solution, (d) the purified conotoxin mr3e, and (e) the conotoxin mr3e generated by the use of the SeODR and TFA/DMSO method 18. Scheme 4 The proposed mechanism for the synthesis of three disulfide bonds in conotoxin mr3e.…”
New methodologies based on benzeneseleninic acid (BSA) were designed to efficiently synthesize multiple disulfide bonds or thioether bridges in peptides in a one-pot manner in which BSA dually functioned as an oxidant and a deprotecting reagent.
“…Regioselectvie synthesis of two disulfide bonds by the use of the BSA-ODr approach Recently, methionine selenoxide (MetSeO) as an oxidation and deprotecting reagent was used to construct two disulfide bonds in peptides (named SeODR) in a one-pot manner in our laboratories. 18 Inspired by the SeODR reaction, we considered that BSA may also be used to regioselectively construct two disulfide bonds in peptides. Thus, the synthesis of two disulfide bonds in α-conotoxin SI was first investigated by reaction of linear α-conotoxin SI-1 with BSA.…”
Section: Resultsmentioning
confidence: 99%
“…It was reported that Br − was a facilitator of the SeODR approach. 18 Thus, the reaction of BSA with oxy (Acm) was also investigated in HBr solution. As expected, oxytocin was successfully generated (entries v-viii).…”
“…4 and S40 †). 18 Next, the synthesis of three disulfide bonds in conotoxin mr3e by the use of the BSA oxidation method was investigated in phosphate buffer. The results are shown in Table S5 † and Fig.…”
Section: Synthesis Of Mbds By the Bsa Oxidation Reactionmentioning
confidence: 99%
“…Fig.5HPLC chromatograms: (a) reduced conotoxin mr3e, (b) reduced conotoxin mr3e was aged for 3 h in pH 7.0 phosphate buffer solution, (c) reduced conotoxin mr3e reacted with BSA for 45 min in pH 7.0 phosphate buffer solution, (d) the purified conotoxin mr3e, and (e) the conotoxin mr3e generated by the use of the SeODR and TFA/DMSO method 18. Scheme 4 The proposed mechanism for the synthesis of three disulfide bonds in conotoxin mr3e.…”
New methodologies based on benzeneseleninic acid (BSA) were designed to efficiently synthesize multiple disulfide bonds or thioether bridges in peptides in a one-pot manner in which BSA dually functioned as an oxidant and a deprotecting reagent.
“…However, these reagents often require long reaction times and/or an excess amount of reagent relative to those of the polypeptides. 13 Thus, the development of techniques to obtain the desired disulfide in high yield and purity remains challenging.…”
A resin-supported cyclic telluride effectively promoted oxidation of thiols in polypeptides as well as small molecules in a solid–liquid biphasic reaction system, providing the corresponding pure disulfide states without a purification process.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.