17554-34-6Relevant articles and documents
Acid-Stable Ester Linkers for the Solid-Phase Synthesis of Immobilized Peptides
Budě?ínsky, Milo?,Jirá?ek, Ji?í,Mitrová, Katarína,Pícha, Jan
, p. 1297 - 1306 (2020/07/04)
A series of N-terminally Fmoc-protected linkers of the general formula Fmoc-X?CO?O?Y?COOH have been prepared, where X is ?NH?CH2?CH2- or -p-(aminomethyl)phenyl- and Y is ?(CH2)n? (n is 1 or 4) or -p-(methyl)phenyl-. These linkers can easily be covalently attached via their C-terminal carboxyl group to a resin bearing a free amino group. After cleavage of the N-terminal Fmoc group, the linkers can be extended by standard solid-phase peptide synthesis techniques. These ester linkers are acid-stable and resistant to the base-mediated diketopiperazine formation that often occurs during the synthesis of ester-bound peptides; they are stable at neutral pH in aqueous buffers for days but can be effectively cleaved with 0.1 m NaOH or aq. ammonia within minutes or hours, respectively. These properties make these ester handles well suited for use as linkers for the solid-phase peptide synthesis of immobilized peptides when the stable on-resin immobilization of the peptides and the testing of their biological properties in aqueous buffers at neutral pH are necessary.
Highly stereoselective peptide modifications through Pd-catalyzed allylic alkylations of chelated peptide enolates
Deska, Jan,Kazmaier, Uli
, p. 6204 - 6211 (2008/02/13)
Deprotonation of peptides in the presence of zinc chloride gives rise to highly reactive nucleophiles that can be subjected to palladium-catalyzed allylic alkylation reactions. Excellent diastereoselectivities are obtained that are nearly independent of the allylic substrate used. By using this protocol, highly functionalized side chains can also be incorporated in excellent yields and selectivities. The stereochemicaloutcome of the reaction is exclusively controlled by the peptide chain as long as terminal π-allyl-palladium complexes are involved. Probably, there is a threefold coordination, at least, ofthe deprotonated peptide chain to the chelating zinc ion. In such metal peptide complexes, one face of the generated enolate is shielded by the side chain of the adjacent amino acid, thus directing the electrophilic attack onto the opposite face. This behavior explains why an S amino acid always generates an R amino acid (and the other way round).
Novel non-peptide GPIIb/IIIa antagonists: Synthesis and biological activities of 2-[4-[2-(4-amidinobenzoylamino)-2-(substituted)acetyl]-3-(2-methoxy-2- oxoethyl)-2-oxopiperazinyl] acetic acids
Kitamura,Fukushi,Miyawaki,Kawamura,Terashita,Sugihara,Naka
, p. 258 - 267 (2007/10/03)
To improve the in vitro and in vivo potency of our first low molecular weight GPIIb/IIIa antagonist 1 (TAK-029), a series of 2-[4-[2-(4-amidinobenzoylamino)-2-(substituted)acetyl]-3-(2-methoxy-2- oxoethyl)-2-oxopiperazinyl]acetic acids were synthesized th
