NDLI: N-Methylation of N $^{α}$-Acetylated, Fully C$^{α}$-Ethylated, Linear Peptides

Content Provider	Springer Nature Link
Author	Moretto, Alessandro Zotti, Marta Crisma, Marco Formaggio, Fernando Toniolo, Claudio
Copyright Year	2008
Abstract	“Mono-N-methyl scan” is a rational approach for the optimization of the peptide biological properties. N-Methylation of the –CONH– functionality is also a useful tool for discriminating solvent exposed from intramolecularly H-bonded secondary amide groups in peptides. We are currently extending this reaction to linear peptides based on C$^{α}$-tetrasubstituted α-amino acids. Following our study on the synthesis and conformation of the mono-N-methylated peptides from C$^{α}$-methylated residues, in this work we investigated the N-methylation reaction on homo-peptides to the pentamer level from the C$^{α}$-ethylated residue C$^{α,α}$-diethylglycine. Under the classical experimental conditions used, exclusively mono-N-methylation (on the N-terminal, acetylated residue) takes place, as unambiguously shown by mass spectrometry, 2D-NMR, and X-ray diffraction techniques. This backbone modification does not seem to involve any significant change in the peptide conformation in the crystalline state.
Starting Page	307
Ending Page	314
Page Count	8
File Format	PDF
ISSN	15733149
Journal	International Journal of Peptide Research and Therapeutics
Volume Number	14
Issue Number	4
e-ISSN	15733904
Language	English
Publisher	Springer Netherlands
Publisher Date	2008-09-12
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	C$^{α}$-Ethylated α-amino acid Fully-extended conformation 3$_{10}$-Helix Peptide N-methylation β-Turn Molecular Medicine Pharmacology/Toxicology Pharmaceutical Sciences/Technology Polymer Sciences Animal Anatomy / Morphology / Histology Biochemistry
Content Type	Text
Resource Type	Article
Subject	Analytical Chemistry Drug Discovery Biochemistry Molecular Medicine Bioengineering

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