Synthesis of protected pseudopeptides from dicarboxylic amino acids by Mitsunobu condensation

Boyarskaya, Natalya P.; Prokhorov, D. I.; Kirillova, Yu. G.; Zvonkova, E. N.; Швец, В. И.

doi:10.1016/j.tetlet.2005.08.121

Cited by 13 publications

(7 citation statements)

References 16 publications

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“…Unfortunately, this approach is inapplicable in the case of L -Glu-based monomers 4 and 5. (Monomolecular cyclization of the pseudopeptides would primarily occur instead of the acylation of the secondary amino groups in the respective pseudopeptides with the carboxymethylated heterocycles [ 59 ]).…”

Section: Resultsmentioning

confidence: 99%

Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding

et al. 2015

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New polyanionic modifications of polyamide nucleic acid mimics were obtained. Thymine decamers were synthesized from respective chiral α- and γ-monomers, and their enantiomeric purity was assessed. Here, we present the decamer synthesis, purification and characterization by MALDI-TOF mass spectrometry and an investigation of the hybridization properties of the decamers. We show that the modified γ-S-carboxyethyl-T10 PNA forms a stable triplex with polyadenine DNA.

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Section: Resultsmentioning

confidence: 99%

Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding

et al. 2015

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“…41 Recently, the seven-member lactam Aia (4-amino-1,2,4,5-tetrahydro-indolo[2,3-c]-azepin-3-one) was introduced into biologically active peptides containing Trp residues by a solid-phase strategy featuring reductive amination using Fmoc-2′-formyl-tryptophan followed by lactam formation. 42 Although several solution-phase methods have been described, [22][23][24]43 to the best of our knowledge, no solidsupported methodology has been reported for Bgl peptide synthesis.…”

Section: Introductionmentioning

confidence: 99%

Positional Scanning for Peptide Secondary Structure by Systematic Solid-Phase Synthesis of Amino Lactam Peptides

et al. 2009

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Incorporation of amino lactams into biologically active peptides has been commonly used to restrict conformational mobility, enhance selectivity, and increase potency. A solid-phase method using a Fmoc-protection strategy has been developed for the systematic synthesis of peptides containing configurationally defined alpha- and beta-amino gamma-lactams. N-Alkylation of N-silyl peptides with five- and six-member cyclic sulfamidates 9 and 8 minimized bis-alkylation and provided N-alkyl peptides, which underwent lactam annulation under microwave heating. Employing this solid-phase protocol on the growth hormone secretagogue GHRP-6, as well as on the allosteric modulator of the IL-1 receptor 101.10, has furnished 16 lactam derivatives and validated the effectiveness of this approach on peptides bearing aliphatic, aromatic, branched, charged, and heteroatomic side chains. The binding affinity IC(50) values of the GHRP-6 lactam analogues on both the GHS-R1a and CD36 receptors are reported as well as inhibition of thymocyte proliferation measurements for the 101.10 lactam analogues. In these cases, lactam analogues were prepared exhibiting similar or improved properties compared with the parent peptide. Considering the potential for amino lactams to induce peptide turn conformations, the effective method described herein for their supported construction on growing peptides, and for the systematical amino lactam scan of peptides, has proven useful for the rapid identification of the secondary structure necessary for peptide biological activity.

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“…In 2005, Boyarskaya et al [32] used the Mitsunobu strategy to overcome the problems associated with the preparation of N -aldehydes from their corresponding dicarboxylic acids (Scheme 8). Glycine, aspartic acid and glutamic acid derivatives were selectively converted into their -amino alcohol derivatives (29) using BH 3 in THF, without the reduction of the benzyl ester group.…”

Section: Synthetic Strategies For the Prepara-tion Of Dipeptides Withmentioning

confidence: 99%

“…As the latter is unstable under acidic conditions, it is easily transformed back to the original vicinal diamine. To achieve an orthogonal protection scheme, a Fmoc protecting group was used for the protection of the N-terminal amino group of glycine (32). This was then converted to the corresponding Weinreb amide (33), which is reduced to the aldehyde (34).…”

Section: Synthetic Strategies For the Prepara-tion Of Dipeptides Withmentioning

confidence: 99%

Recent Advances in the Synthesis and Applications of Reduced Amide Pseudopeptides

Živec¹,

Gobec

2009

CMC

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Being one of the simplest and widely used isosteric replacements for the peptide bond, reduced amide has been successfully applied in the synthesis of many bioactive compounds. The introduction of reduced amide not only confers the pseudopeptide a higher enzymatic resistance and a linear and more flexible structure, but also increases its hydrophylicity due to the introduction of a protonable group. It has also proved adequate as a transition state mimetic for the tetrahedral intermediate formed during the hydrolysis of the peptide bond. Recent advances in the solution and solid-phase synthesis of reduced amides that emerged during the past ten years are presented. Most of them include the use of microwave irradiation to shorten the reaction times and improve the yields. The bioorganic chemistry of reduced-peptide-containing compounds represents an area of growing interest and it has recently been expanded to include analogues of endogenous peptides/ hormones that are resistant to hydrolysis by serum peptidases and enzyme inhibitors. Under certain conditions, synthetic peptides are highly immunogenic in animals, and might constitute chemically defined, safe and cheap vaccines. Linear pseudooligolysines, containing multiple adjacent CH2NH amide bond are potential candidates for future use as DNA carriers in gene delivery. Reduced amides have also seen use in the preparation of peptide nucleic acids and antibacterial peptides.

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Synthesis of protected pseudopeptides from dicarboxylic amino acids by Mitsunobu condensation

Cited by 13 publications

References 16 publications

Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding

Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding

Positional Scanning for Peptide Secondary Structure by Systematic Solid-Phase Synthesis of Amino Lactam Peptides

Recent Advances in the Synthesis and Applications of Reduced Amide Pseudopeptides

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