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Consecutive Ribosomal Incorporation of α-Aminoxy/α-Hydrazino Acids with l/d-Configurations into Nascent Peptide Chains.
J Am Chem Soc
November 2021
Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
α-Aminoxy and α-hydrazino acids are β-amino acid analogs with β-carbons replaced by oxygen and nitrogen, respectively. Such heteroatoms dictate the folding of peptides into specific secondary structures called pseudo-γ-turns. Achiral α-aminoxyacetic acid (Gly) and l-α-hydrazinophenylalanine (l-Phe) have been shown to be suitable for single incorporation during ribosomal translation, but whether ribosomes tolerate other types of α-aminoxy/α-hydrazino acids with l/d-configurations is unknown.
View Article and Find Full Text PDFN-Hydroxy peptides: solid-phase synthesis and β-sheet propensity.
Org Biomol Chem
May 2020
Department of Chemistry & Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Peptide backbone amide substitution can dramatically alter the conformational and physiochemical properties of native sequences. Although uncommon relative to N-alkyl substituents, peptides harboring main-chain N-hydroxy groups exhibit unique conformational preferences and biological activities. Here, we describe a versatile method to prepare N-hydroxy peptide on solid support and evaluate the impact of backbone N-hydroxylation on secondary structure stability.
View Article and Find Full Text PDFThe impact of α-hydrazino acids embedded in short fluorescent peptides on peptide interactions with DNA and RNA.
Org Biomol Chem
June 2016
Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia.
A series of novel hydrazino-based peptidomimetics and analogues comprising N-terminal lysine and C-terminal phenanthridinyl-l-alanine were prepared. The presented results demonstrate the up to now unknown possibility to finely modulate peptide interactions with DNA/RNA by α-hydrazino group insertion and how the different positioning of two α-hydrazino groups in peptides controls binding to various double stranded and single stranded DNA and RNA. All peptidomimetics bind with 1-10 micromolar affinity to ds-DNA/RNA, whereby the binding mode is a combination of electrostatic interactions and hydrophobic interactions within DNA/RNA grooves.
View Article and Find Full Text PDFSynthesis of aromatic sphingosine analogues by diastereoselective amination of enantioenriched trans-γ,δ-unsaturated β-hydroxyesters.
J Org Chem
August 2014
Department of Chemistry and Biochemistry, Institute of Arctic Biology, University of Alaska, Fairbanks, Alaska 99775, United States.
An effective route to N-Boc-protected aromatic sphingosine analogues is accomplished. The strategy is based on the diastereoselective amination of enantioenriched trans-γ,δ-unsaturated β-hydroxyesters to establish anti,N-Boc-α-hydrazino-β-hydroxyesters. Nonreductive E1cB elimination is essential for the successful N-N bond cleavage of hydrazine while preserving the trans double bond.
View Article and Find Full Text PDFAsymmetric NHC-catalyzed redox α-amination of α-aroyloxyaldehydes.
Org Lett
December 2013
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, United Kingdom.
Asymmetric α-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of α-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form α-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N-N bond cleavage.
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