Deprotection of S‑Acetamidomethyl
and 1,3-Thiazolidine-4-Carbonyl
Protecting Groups from Cysteine Side Chains in Peptides by trans-[PtX2(CN)4]2–: One-Pot Regioselective Synthesis of Disulfide Bonds
Posted on 2022-01-05 - 15:03
In
this study, we developed an efficient approach for disulfide
bond formation in peptides utilizing the Pt(IV) complex trans-[PtBr2(CN)4]2– to mediate
Acm and Thz deprotections. [PtBr2(CN)4]2– can oxidatively deprotect two Acm groups or deprotect
one Thz group and one Acm group to directly form an intramolecular
disulfide bond in peptides. Several disulfide-containing peptides
with excellent yields were achieved via the deprotection method in
an aqueous medium under aerobic conditions. Kinetic studies indicated
that the dominant path of the reaction is of first-order in both [Pt(IV)]
and [peptide]; moreover, the deprotection rate increased dramatically
with the addition of NaBr. A mechanism including a bromide-bridge-mediated
electron transfer process was proposed. Apamin, α-conotoxin
SI, and the parallel homodimer of oxytocin, all containing two disulfide
bonds, were synthesized regioselectively through a one-pot method
by the combined use of the above deprotection approach with oxidants l-methionine selenoxide and [PtBr2(CN)4]2–. All of the reactions were completed within
30 min to afford good yields for these peptides.
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Ma, Dongying; Sun, Jingjing; Shen, Shigang; Chen, Hua; Xu, Wenzhi; Wang, Yafang; et al. (2022). Deprotection of S‑Acetamidomethyl
and 1,3-Thiazolidine-4-Carbonyl
Protecting Groups from Cysteine Side Chains in Peptides by trans-[PtX2(CN)4]2–: One-Pot Regioselective Synthesis of Disulfide Bonds. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.1c02793