64987-82-2Relevant articles and documents
Chemoselective Peptide Cyclization and Bicyclization Directly on Unprotected Peptides
Zhang, Yue,Zhang, Qing,Wong, Clarence T. T.,Li, Xuechen
, p. 12274 - 12279 (2019)
Cyclic peptides are drawing wide attention as potential medium-sized modulators of biomolecular interactions with large binding surfaces. Simple but effective peptide cyclization methods are needed to construct cyclic peptide libraries by both peptide and nonpeptide chemists. Herein, we report a highly chemoselective and operation-simple method directly cyclizing unprotected peptides, in which ortho-phthalaldehyde (OPA) is found to react with the lysine/N-terminus and cysteine within one unprotected peptide sequence effectively to form the isoindole-bridged cyclic peptides. This reaction is carried out in the aqueous buffer and features tolerance of diverse functionalities, rapid and clean transformation, and operational simplicity. In addition, OPA peptide cyclization can also be combined with native chemical ligation-mediated cyclization to generate bicyclic peptides. Furthermore, the OPA peptide cyclization product can further react with the N-maleimide moiety in a one-pot manner to introduce additional functional motifs, like a fluorophore probe, biomolecules (e.g., glycan, peptide, or DNA). This OPA-cyclization method extends the toolbox for integrating postcyclization modification and bioconjugation into peptide cyclization with an all-in-one manner strategy.
One-pot synthesis of succinimidyl-4-(N-maleimidomethyl)cyclohexane-1- carboxylate (SMCC)
Leonard, Nicholas M.,Brunckova, Jarmila
, p. 180 - 183 (2012)
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One-pot solvent free, green route to novel substituted spiro[oxindole-isoxazolidine] derivatives: novel candidates as antimicrobial agents
KAUR, MANPREET,BHATIA, SUMEET KAUR,SINGH, BALDEV
, p. 1299 - 1303 (2021/06/09)
The environmentally benign catalyst and solvent-free synthesis of ketonitrones may not always be accomplished by simple condensation reactions. The occasional reports of green synthetic routes toward these compounds have been reported. The key features of
CYCLIC COMPOUNDS AND METHODS OF MAKING AND USING
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Page/Page column 110, (2020/10/19)
Disclosed are compounds and methods for highly effective chemoselective peptide cyclization and bicyclization directly on unprotected peptides and other compounds as well as the compounds produced by the methods, which have a novel structural motif. The fast reaction rate and operational simplicity render this method to be highly effective to synthesize cyclic structures, i.e. cyclic peptides. The cyclic compounds allow for various functionalities useful in chemical biology study and drug discovery.
