On-Resin Macrocyclization of Peptides Using Vinyl Sulfonamides as a Thiol-Michael “Click” Acceptor
نویسندگان
چکیده
منابع مشابه
On-resin peptide macrocyclization using thiol-ene click chemistry.
A versatile and rapid synthetic strategy has been developed for the on-resin cyclization of peptides using thiol-ene photochemistry. This unique method exploits the thiol group of natural cysteine amino acids and allows for various alkenes to be incorporated orthogonal to the peptide backbone.
متن کاملMultifunctional monomers based on vinyl sulfonates and vinyl sulfonamides for crosslinking thiol-Michael polymerizations: monomer reactivity and mechanical behavior.
Multifunctional vinyl sulfonates and vinyl sulfonamides were conveniently synthesized and assessed in thiol-Michael crosslinking polymerizations. The monomer reactivities, mechanical behavior and hydrolytic properties were analyzed and compared with those of analogous thiol-acrylate polymerizations. Materials with a broad range of mechanical properties and diverse hydrolytic stabilities were ob...
متن کاملFacile Image Patterning via Sequential Thiol−Michael/Thiol−Yne Click Reactions
Freestanding substrates with high refractive index modulation, good oxygen resistance, and low volume shrinkage are critical in photolithography for the purpose of high density data storage, image patterning and anticounterfeiting. Herein, we demonstrate a novel paradigm of direct holographic image patterning via the radical-mediated thiol− yne click reaction subsequent to the base-catalyzed th...
متن کاملEnzyme-Catalyzed Macrocyclization of Long Unprotected Peptides
A glutathione S-transferase (GST) catalyzed macrocyclization reaction for peptides up to 40 amino acids in length is reported. GST catalyzes the selective S(N)Ar reaction between an N-terminal glutathione (GSH, γ-Glu-Cys-Gly) tag and a C-terminal perfluoroaryl-modified cysteine on the same polypeptide chain. Cyclic peptides ranging from 9 to 24 residues were quantitatively produced within 2 h i...
متن کاملEnantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging Michael acceptors.
Chiral framework: Chiral amines with pyrrolidine frameworks catalyze the enantioselective conjugate addition of a wide range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99 % ee (see scheme). The high versatility of the Michael adducts is exemplified by various functionalizations with conservation of the optical purity.Chiral ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Bioconjugate Chemistry
سال: 2018
ISSN: 1043-1802,1520-4812
DOI: 10.1021/acs.bioconjchem.8b00751