79775-03-4Relevant academic research and scientific papers
An activated phosphate for an efficient amide and peptide coupling reagent
Yasuhara, Tomohisa,Nagaoka, Yasuo,Tomioka, Kiyoshi
, p. 2901 - 2902 (2000)
An activated phosphate for an efficient amide and peptide coupling reagent was discussed. Activation of diethyl phosphates was realized by attaching trifluoromethanesulfonanilide as an efficient leaving group and the phosphate proved to be a promising amide and peptide coupling reagent. Results showed that reactions of a primary amine with α-branched carboxylic acids and benzoic acid gave within 1 h the amides in quite high yield.
Helical Peptides Design for Molecular Dipoles Functionalization of Wide Band Gap Oxides
Bartynski, Robert A.,Chen, Yuan,Galoppini, Elena,Harmer, Ryan,Rangan, Sylvie,Viereck, Jonathan
supporting information, p. 3489 - 3498 (2020/03/06)
The use of helical hexapeptides to establish a surface dipole layer on a TiO2 substrate, with the goal of influencing the energy levels of a coadsorbed chromophore, is explored. Two helical hexapeptides, synthesized from 2-amino isobutyric acid
Deracemization and the first CD spectrum of a 310-helical peptide made of achiral α-amino-isobutyric acid residues in a chiral membrane mimetic environment
Ceccacci, Francesca,Mancini, Giovanna,Rossi, Paola,Scrimin, Paolo,Sorrenti, Alessandro,Tecilla, Paolo
supporting information, p. 10133 - 10135 (2013/10/22)
Interaction of the racemic helical homo-octapeptide made by the achiral Cα-methyl alanine (Aib) amino acid with a chiral enantiopure micellar aggregate made of N-dodecylproline led to the deracemization of the helical Aib sequence thus allowing
N-lipidated oligopeptides immobilized on cellulose as new type of organocatalysts
Fraczyk, Justyna,Kolesinska, Beata,Kaminski, Zbigniew J.
, p. 562 - 571 (2013/09/12)
A library of supramolecular structures formed by self-organization of N-lipidated tripeptides, dipeptides and Nacylated amino acids attached to cellulose according to the TASP concept via aminophenylamino-1,3,5-triazine was synthesized and the catalytic a
Synthesis of poly-aib oligopeptides and aib-containing peptides via the 'azirine/oxazolone method', and their crystal structures
Dannecker-Doerig, Ingeborg,Linden, Anthony,Heimgartner, Heinz
, p. 993 - 1011 (2011/08/05)
The protected poly-Aib oligopeptides Z-(Aib)n-N(Me)Ph with n=2-6 were prepared according to the 'azirine/oxazolone method', i.e., by coupling amino or peptide acids with 2,2,N-trimethyl-N-phenyl-2H-azirin-3-amine (1a) as an Aib synthon (Schemea 2). Following the same concept, the segments Z-(Aib)3-OH (9) and H-L-Pro-(Aib)3-N(Me)Ph (20) were synthesized, and their subsequent coupling with N,N′- dicyclohexylcarbodiimide (DCC)/ZnCl2 led to the protected heptapeptide Z-(Aib)3-L-Pro-(Aib)3-N(Me)Ph (21; Schemea 3). The crystal structures of the poly-Aib oligopeptide amides were established by X-ray crystallography confirming the 310-helical conformation of Aib peptides.
Influence of glycosylation on the conformational preferences of folded oligopeptides
Gobbo, Marina,Nicotra, Alessia,Rocchi, Raniero,Crisma, Marco,Toniolo, Claudio
, p. 2433 - 2443 (2007/10/03)
Synthesis, characterization, and conformational analysis by FT-IR absorption, 1H NMR and X-ray diffraction techniques are described for a series of side-chain O-glycosylated Thr peptides of different main-chain length rich in the helicogenic Aib residue. The results obtained, compared with those of related peptides containing side-chain protected Thr and Ser residues and host Aib homo-oligomers, also reported in this work, provided new information on the preferred conformation of the naturally occurring antifreeze glycopeptides.
Emerimicins III and IV and their ethylalanine12 epimers. Facilitated chemical-enzymatic synthesis and a qualitative evaluation of their solution structures
Slomczynska, Urszula,Beusen, Denise D.,Zabrocki, Janusz,Kociolek, Karol,Redlinski, Adam,Rensser, Fritz,Hutton, William C.,Leplawy, Miroslaw T.,Marshall, Garland R.
, p. 4095 - 4106 (2007/10/02)
The peptaibol antibiotics, emerimicin III and IV (Ac-Phe1-MeA2-MeA3-MeA4-VaI 5-Gly6-Leu7-MeA8-MeA 9-Hyp10-Gln11-R-EtA12-Hyp
Determination of an 8-? interatomic distance in a helical peptide by solid-state NMR spectroscopy
Holl, Susan M.,Marshall, Garland R.,Beusen, Denise D.,Kociolek, Karol,Redlinski, Adam S.,Leplawy, Miroslaw T.,McKay, Robert A.,Vega, Shimon,Schaefer, Jacob
, p. 4830 - 4833 (2007/10/02)
The combination of transferred-echo double resonance (TEDOR) with rotational-echo double resonance (REDOR) has been used to measure an 8-? fluorine-carbon internuclear distance in a nine-residue fragment of the peptide antibiotic emerimicin. The fragment is 19FCH2CO-Phe-MeA-MeA-[1-13C]MeA-[ 15N]Val-Gly-Leu-MeA-MeA-OBzl (MeA = α-methylalanine or aminoisobutyric acid). The TEDOR part of this magic-angle-spinning, solid-state NMR experiment selects the 13C label by its dipolar coupling to 15N and suppresses the natural-abundance carbon background. The REDOR part of the experiment measures dipolar coupling of the selected carbon to 19F. The TEDOR-REDOR combined experiment works with a variety of spin 1/2 nuclei and can be used to characterize internuclear distances and geometry in macromolecular aggregates that do not crystallize.
3-(Dimethylamino)-2,2-dimethyl-2H-azirine as an Aib Equivalent; Synthesis of Aib Oligopeptides
Obrecht, Daniel,Heimgartner, Heinz
, p. 102 - 115 (2007/10/02)
3-(Dimethylamino)-2,2-dimethyl-2H-azirine (1) reacts with carboxylic acids at 0-25 degC to give 2-acylamino-N,N,2-trimethylpropionamides (=2-acylamino-N,N-dimethylisobutyramide, acyl-Aib-NMe2) in excellent yields (Scheme 2 and 3).Examples of α-amino-, α-h
Linear Oligopeptides. Part 147. Chemical and Crystallographic Study of the Reaction between Benzyloxycarbonyl Chloride and α-Aminoisobutyric Acid
Valle, Giovanni,Formaggio, Fernando,Crisma, Marco,Bonora, Gian Maria,Toniolo, Claudio,et al.
, p. 1371 - 1376 (2007/10/02)
From the reaction mixture of benzyloxycarbonyl chloride and α-aminoisobutyric acid three crystalline compounds were isolated and characterized by chromatographic and spectroscopic techniques and X-ray diffraction.Two of them are polymorphic forms of the N
