About: Regioselective incorporation of backbone constraints compatible with traditional solid-phase peptide synthesis

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About: Regioselective incorporation of backbone constraints compatible with traditional solid-phase peptide synthesis Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	A protected aldehyde was attached via a two-carbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile. A protected aldehyde was attached via a two-carbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile. (en)
Title	Regioselective incorporation of backbone constraints compatible with traditional solid-phase peptide synthesis Regioselective incorporation of backbone constraints compatible with traditional solid-phase peptide synthesis (en)
skos:prefLabel	Regioselective incorporation of backbone constraints compatible with traditional solid-phase peptide synthesis Regioselective incorporation of backbone constraints compatible with traditional solid-phase peptide synthesis (en)
skos:notation	RIV/61989592:15310/13:33147703!RIV14-GA0-15310___
http://linked.open...avai/predkladatel	Přírodovědecká fakulta
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(EE2.3.20.0009), P(GAP207/12/0473), P(ME09057)
http://linked.open...iv/cisloPeriodika	1
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Vaňková, Barbora Krchňák, Viktor La Venia, Agustina
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Palackého v Olomouci / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	102023
http://linked.open...ai/riv/idVysledku	RIV/61989592:15310/13:33147703
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	iminium, bisheterocycles, solid-phase synthesis, regioselectivity (en)
http://linked.open.../riv/klicoveSlovo	solid-phase synthesis regioselectivity bisheterocycles iminium
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[8D2E4283E3FE]
http://linked.open...i/riv/nazevZdroje	ACS Combinatorial Science
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...vavai/riv/projekt	Research of new organic compounds with anticancer activity with use of combinatorial chemistry Syntéza diverzních peptidomimetik s rigidní strukturou na pevné fázi. Combinatorial chemistry in research and education
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	15
http://linked.open...iv/tvurceVysledku	Krchňák, Viktor Lemrová, Barbora La Venia, Agustina
http://linked.open...ain/vavai/riv/wos	000313605600008
issn	2156-8952
number of pages	14 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/co300125m
http://localhost/t...ganizacniJednotka	15310

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