Synthesis of the β-amyloid fragment 5RHDSGY10 and its isomers

Aleshina, E. Yu.; Pyndyk, N. V.; Moisa, A. A.; Sanzhakov, M. A.; Kharybin, Oleg N.; Nikolaev, E. N.; Колесанова, Е. Ф.

doi:10.1134/s1990750808030098

Cited by 2 publications

(4 citation statements)

References 11 publications

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“…The presence of lysine allows this peptide to be acylated at its less hydrophobic C-terminus with a lipophilic adjuvant through the ε-amino group of lysine, provided it is blocked by a selectively removable protective group. The peptide was obtained by solid-phase synthesis on Rink amide resin according to the Fmoc protocol by the method of in situ activated esters [28,29]. After synthesis, the peptide was purified by reversed phase high-performance liquid chromatography (RP-HPLC) using UV and mass-spectrometric detection to identify the target peptide and impurities.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Analysis of Properties of an Immunogenic Fragment from NS4A Polypeptide of Hepatitis C Virus

et al. 2021

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Abstract— The work is aimed at the synthesis and analysis from NS4A of hepatitis C virus (HCV) antigen peptide fragment that contains a conserved B-cell and T-helper epitopes. The 24-mer peptide VIVGRIILSGRPAVIPDREVLYRK-NH2, which contains the main immunogenic site 24–46 of HCV NS4A antigen (corresponding to the 1681–1703 amino acid residues of the HCV polypeptide), subtype 1b, has been prepared via solid-phase synthesis according to the Fmoc-protocol. Particles with diameters of 73 ± 10 nm (30%) and 236 ± 5 nm (70%) have been detected in the water solution of the highly purified peptide (0.5 mg/mL) by dynamic light scattering. The polydispersity index of 0.377 ± 0.012 implies the existence of heterogeneity because of the aggregation of the peptide molecules. The ζ-potential of the peptide aggregates has been determined as 7.0 ± 0.5 mV by means of electrophoretic light scattering. These data confirm the possibility for the development of a nanoscale liposome form of the peptide preparation. Immunoreactivity of the synthesized highly purified peptide has been studied with the use of blood sera of patients with chronic hepatitis C. Antipeptide immunoglobulins G have been detected in 41.7% of serum samples. Thus, this peptide has been shown to reproduce at least one B-epitope, to which antibodies are raised during natural HCV infection. The synthesized 24-mer peptide is a promising candidate for further research and for use as a potential immunogen for the design of a nanoscale therapeutic immunogenic liposomal peptide composition with synthetic lipids as an adjuvant.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Analysis of Properties of an Immunogenic Fragment from NS4A Polypeptide of Hepatitis C Virus

et al. 2021

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“…Tertiary amine DBU was used as a more efficient catalyst of the hydroxycarbonyl dibenzofulvene detachment from the peptide α -amino group, in addition to 4MPIP [31]. Since DBU actively catalyzes the formation of aspartimides, Asp piperidines, Asp epimerization, and Asn dehydration [23, 31, 36], it was not added to the Fmoc removal reagent after Asp or Asn introduction to the growing peptide chains. HATU, HBTU, and HCTU were employed as more efficient acylation activators, among which HATU is the most and HBTU is the least (close to DIC) efficient.…”

Section: Resultsmentioning

confidence: 99%

“…Hence the DBU addition to 4MPIP or piperidine can be recommended as a modification of the standard procedure of multiple parallel peptide synthesis on pins, in order to obtain a unified procedure that allows the correct synthesis of “difficult” peptides. The only problem of DBU usage is its ability to catalyze aspartimide formation from Asp [36]. However, certain side-chain carboxyl protection groups greatly reduce [43–46], and Asp-X peptide bond modifications exclude this side reaction [25, 33, 46], hence permitting the use of more efficient Fmoc removal catalyst in a greater set of difficult synthesis cases.…”

Section: Discussionmentioning

confidence: 99%

“…The choice of hepatitis C virus envelope protein sites for scanning and the preparation of the peptide list were described elsewhere [7, 9]. The peptide synthesis from Fmoc-amino acids using DIPC as the condensation catalyst, as described in the “Mimotopes” manual and [22], was chosen as a standard procedure, except that 4-methyl-piperidine (4MPIP) was employed instead of piperidine [36, 37] and NMP was used as the Fmoc removal and amino acid attachment solvent instead of DMF [38]. …”

Section: Methodsmentioning

confidence: 99%

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Development of the Schedule for Multiple Parallel “Difficult” Peptide Synthesis on Pins

Колесанова

Sanzhakov

Kharybin

2013

International Journal of Peptides

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Unified schedule for multiple parallel solid-phase synthesis of so-called “difficult” peptides on polypropylene pins was developed. Increase in the efficiency of 9-fluorenyl(methoxycarbonyl) N-terminal amino-protecting group removal was shown to have a greater influence on the accuracy of the “difficult” peptide synthesis than the use of more efficient amino acid coupling reagents such as aminium salts. Hence the unified schedule for multiple parallel solid-phase synthesis of “difficult” peptides included the procedure for N-terminal amino group deprotection modified by applying a more efficient reagent for the deprotection and the standard procedure of amino acid coupling by carbodiimide method with an additional coupling using aminium salts, if necessary. Amino acid coupling with the help of carbodiimide allows to follow the completeness of the coupling via the bromophenol blue indication, thus providing the accuracy of the synthesis and preventing an overexpenditure of expensive reagents. About 100 biotinylated hepatitis C virus envelope protein fragments, most of which represented “difficult” peptides, were successfully obtained by synthesis on pins with the help of the developed unified schedule.

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Synthesis of the β-amyloid fragment 5RHDSGY10 and its isomers

Cited by 2 publications

References 11 publications

Synthesis and Analysis of Properties of an Immunogenic Fragment from NS4A Polypeptide of Hepatitis C Virus

Synthesis and Analysis of Properties of an Immunogenic Fragment from NS4A Polypeptide of Hepatitis C Virus

Development of the Schedule for Multiple Parallel “Difficult” Peptide Synthesis on Pins

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