215254-90-3Relevant academic research and scientific papers
Stabilization of Cyclic β-Hairpins by Ugi-Reaction-Derived N-Alkylated Peptides: The Quest for Functionalized β-Turns
Ricardo, Manuel G.,Vasco, Aldrin V.,Rivera, Daniel G.,Wessjohann, Ludger A.
supporting information, p. 7307 - 7310 (2019/10/02)
A solid-phase approach including on-resin Ugi reactions was developed for the construction of β-hairpins. Various N-alkylated dipeptide fragments proved capable of aligning antiparallel β-sheets in a macrocyclic scaffold, thus serving as β-hairpin templates. Gramicidin S was used as the model β-hairpin to compare the Ugi-derived β-turns with the type-II′ β-turn. The results show that the multicomponent incorporation of such N-alkylated residues allows for the simultaneous stabilization and exo-cyclic functionalization of cyclic β-hairpins.
Synthesis and structural characterization of monomeric and dimeric peptide nucleic acids prepared by using microwave-promoted multicomponent reactions
Ovadia, Reuben,Lebrun, Aurélien,Barvik, Ivan,Vasseur, Jean-Jacques,Baraguey, Carine,Alvarez, Karine
, p. 11052 - 11071 (2015/11/25)
A solution phase synthesis of peptide nucleic acid monomers and dimers was developed by using microwave-promoted Ugi multicomponent reactions. A mixture of a functionalized amine, a carboxymethyl nucleobase, paraformaldehyde and an isocyanide as building blocks generates PNA monomers which are then partially deprotected and used in a second Ugi 4CC reaction, leading to PNA dimers. Conformational rotamers were identified by using NMR and MD simulations.
Photocaging of carboxylic acids: A modular approach
Szymanski, Wiktor,Velema, Willem A.,Feringa, Ben L.
supporting information, p. 8682 - 8686 (2014/08/18)
Photocaged compounds are important tools for studying and regulating multiple processes, including biological functions. Reported herein is the use of the Passerini multicomponent reaction for modular preparation of photocaged carboxylic acids. The reaction is compatible with several functionalities and proceeds smoothly both in water and dichloromethane. The choice of aldehyde determines the wavelength used for deprotection and enables formation of orthogonally protected products. The isocyanide component can be used for introduction of reactive tags and photosensitizers, as well as for immobilization on a solid support.
A Straightforward Approach towards Cyclic Photoactivatable Tubulysin Derivatives
Hoffmann, Judith,Kazmaier, Uli
supporting information, p. 11356 - 11360 (2016/02/18)
The development of a new photolabile protecting group containing an additional allyl functionality allows the synthesis of cyclic photoactivatable natural products. Cyclization occurs between the allyl moiety in the protecting group and a second double bond in the target molecule by means of ring-closing metathesis. Cyclization should increase the metabolic stability towards proteases. On the other hand, the conformational change should cause diminished biological activity. As illustrated for tubulysin derivatives, cyclic and photoactivatable drug candidates can easily be obtained in only two steps from simple building blocks through Ugi reaction and ring-closing metathesis. The photolabile protecting group is introduced by means of the isocyanide component during the Ugi reaction.
Synthesis of PNA monomers and dimers by ugi four-component reaction
Xu, Ping,Zhang, Ting,Wang, Wenhao,Zou, Xiaomin,Zhang, Xin,Fu, Yiqiu
, p. 1171 - 1176 (2007/10/03)
Peptide nucleic acids (PNA) have received great attention as tools in molecular biology and biotechnology, diagnostic agents, and potential antisense drugs. Many derivatives and analogues of PNA were designed and prepared to improve their physico-chemical
