Infrared spectra of amino acid and peptide monoderivatives of [60]fullerene and their methyl esters

Klemenkova, Zinaida S.; Романова, В. С.; Tsyryapkin, V. A.; Muradan, Vyacheslav E.; Парнес, З. Н.; Локшин, Б. В.; Vol'pin, M. E.

doi:10.1070/mc1996v006n02abeh000580

Cited by 14 publications

(3 citation statements)

References 9 publications

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“…9 The IR spectra of the synthesized AFDs (KBr pellets) con tain intense absorption bands in the ranges 1590-1620 and 1350-1420 cm -1 assigned to asymmetric and symmetric stretch ing vibrations of the carboxyl group (СОО -,  аs (СОО -), and  s (СОО -)). 10 This proves that an ADF molecule includes a zwiterionic form with the ionized carboxy group. In addition, the IR spectra of thus obtained ADFs are characterized by broad absorption bands with a maximum about 3200 cm -1 .…”

Section: Methodsmentioning

confidence: 92%

Design of a hybrid nanostructure based on fullerene C60 and biologically active substance for modeling physiological properties of compounds

et al. 2014

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The effects of cognitive stimulating substance BD 2 of the  carboline family and a hybrid compound based on fullerene С 60 and attached BD 2 on various aspects of the behavior of animals were studied. The synthesized hybrid fullerene compound (HFC) has no side psycho stimulating effect characteristic of BD 2 but fully retains the properties of a cognitive stimulat ing agent. The design of hybrid compounds based on fullerene С 60 and pharmacologically active groups can be one of the ways for optimizing therapeutically promising compounds.

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Section: Methodsmentioning

confidence: 92%

Design of a hybrid nanostructure based on fullerene C60 and biologically active substance for modeling physiological properties of compounds

et al. 2014

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“…The [60]fullerene containing peptides have been generally characterized by matrix assisted laser desorption/ionization (MALDI) mass spectrometry by the presence of the M + , M + +H, or M + +Na ions, depending on the reaction conditions 31,36 . In some cases, the [60]fullerene-functionalized peptides are sufficiently soluble in H 2 O to provide a UV-visible spectrum 36 , while IR spectroscopy shows the functionalization of the C 60 39 . However, it is the effect of the hydrophobic C 60 moiety on the peptide configuration that is of interest.…”

Section: Structural Effectsmentioning

confidence: 99%

[60]Fullerene-peptides: bio-nano conjugates with structural and chemical diversity

Barron

2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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[60]Fullerene-peptides represent a simple yet chemically diverse example of a bio-nano conjugate. The C moiety provides the following attributes to the conjugate: (a) precise three-dimensional architecture, (b) a large hydrophobic mass and (c) unique electronic properties. Conversely, the peptide component provides: (a) structural diversity depending on the overall length and amino acids composition, (b) charge flexibility and (c) secondary structure and recognition. Recent advances in the synthetic strategy for [60]fullerene-peptide synthesis from both pre-formed peptides and using solid phase peptide synthesis (SPPS) are described. The effects of the hydrophobic C on the secondary structure of the peptide depend on the sequence of the latter, but in general the relative stability of particular structures is greatly enhanced. The ability of the [60]fullerene substituent to dramatically modify both cellular uptake and transdermal transport is discussed as is the effects on cell viability and antimicrobial activity.

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“…Thus, C 60 -amino acids 6 were synthesized by alkylation of a Schiff base derived from glycine (or a chiral nickel complex) with the [60]fullerene used as an electrophilic reagent. On the other hand, the reaction of amino acids with the [60]fullerene could be performed by hydroamination or nitrene addition to afford derivatives 7 or 8 , respectively. Finally, amino acid derivatives 9 – 11 were obtained via dipolar or Diels–Alder cycloadditions with [60]fullerene. − It should be highlighted that fulleroproline derivatives 10 are obtained in high ee by an efficient asymmetric 1,3-dipolar cycloaddition of Schiff bases with [60]fullerene catalyzed by chiral silver or gold complexes .…”

Section: Introductionmentioning

confidence: 99%

[60]Fullerene l-Amino Acids and Peptides: Synthesis under Phase-Transfer Catalysis Using a Phosphine–Borane Linker. Electrochemical Behavior

et al. 2017

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A new method to link amino acid and peptide derivatives to [60]fullerene is described. It uses hydrophosphination with a secondary phosphine borane. First, the stereoselective synthesis of secondary phosphine borane amino acid derivatives was achieved by alkylation of phenylphosphine borane with γ-iodo-α-amino ester reagents under phase-transfer catalysis (PTC). Second, a sec-phosphine borane amino ester was saponified and coupled with α,γ-diamino esters to afford the corresponding dipeptide derivatives in good yields. Finally, the hydrophosphination reaction of [60]fullerene by the sec-phosphine borane compounds was performed under PTC to obtain C-amino acid or dipeptide derivatives in yields up to 80% by P-C bond formation. This addition reaction which proceeds in mild and moderate dilute conditions (0.03 M) leads to [60]fullerene derivatives as epimeric mixtures (∼1:1) due to the P-chirogenic center but without racemization of the amino acid or peptide moiety. In addition, the electrochemical behavior of a C-phosphine borane amino ester was investigated by cyclic voltammetry and spectroelectrochemistry after controlled-potential electrolysis. It showed evidence for the retro-hydrophosphination reaction into free [60]fullerene and sec-phosphine borane amino ester compound. Consequently, the synthesis of sec-phosphine borane amino acids followed by their use in hydrophosphination reactions of [60]fullerene under phase-transfer catalysis has demonstrated a great utility for the preparation of C-derivatives. Indeed, the hydrophosphination and the retro-hydrophosphination reactions of [60]fullerene/phosphine borane compounds offer a promising new strategy for the reversible immobilization of amino acid or peptide derivatives on carbon nanomaterials such as [60]fullerene.

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Infrared spectra of amino acid and peptide monoderivatives of [60]fullerene and their methyl esters

Cited by 14 publications

References 9 publications

Design of a hybrid nanostructure based on fullerene C60 and biologically active substance for modeling physiological properties of compounds

Design of a hybrid nanostructure based on fullerene C60 and biologically active substance for modeling physiological properties of compounds

[60]Fullerene-peptides: bio-nano conjugates with structural and chemical diversity

[60]Fullerene l-Amino Acids and Peptides: Synthesis under Phase-Transfer Catalysis Using a Phosphine–Borane Linker. Electrochemical Behavior

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