Synthesis of phosphorylated dehydrotyrosine-containing tripeptides from 5-amino-2-aminoalkyl-1,3-oxazole-4-phosphonic acids derivatives

Lukashuk, E. I.; Abdurakhmanova, E. R.; Kondratyuk, K. M.; Golovchenko, A. V.; Броварец, В. С.

doi:10.1134/s1070363215010120

Cited by 3 publications

(3 citation statements)

References 9 publications

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“…Availability of the latter ones opened an original route to structurally variable phosphonopeptides 35 and 36. [49][50][51][52][53] A preliminary study on the addition of thiols and amines to double bonds of quite readily affordable phosphono dehydropeptide 37 (Fig. 12) indicated that this procedure could be a new mean to produce phosphono peptides containing nontypical side chains (compounds 38 and 39).…”

Section: B Peptides Containing C-terminal Aminophosphonic Acidsmentioning

confidence: 99%

Phosphonopeptides containing free phosphonic groups: recent advances

Kafarski

2020

RSC Adv.

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Section: B Peptides Containing C-terminal Aminophosphonic Acidsmentioning

confidence: 99%

Phosphonopeptides containing free phosphonic groups: recent advances

Kafarski

2020

RSC Adv.

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“…The azlactone approach makes it possible to purposefully introduce dehydrtyrozine fragment into phosphorylated peptidomimetics. Thus, 1,3-oxazole derivatives 39 were obtained by reacting of 4-phosphorylated derivatives of 5-amino-2-aminoalkyl-1,3-oxazole 20a, 37 with 4-(4-acetoxybenzylidene)-2-phenyl-1,3-oxazol-5-one 38 [29] (Scheme 9). Further compounds 39 were transformed into phosphorylated tripeptides 40 on heating in a mixture of acetic acid-water (5 : 1).…”

Section: Synthesis On the Base Of Aromatic 13-oxazolesmentioning

confidence: 99%

1,3-Oxazoles as precursors of phosphorylated amino acids and peptidomimetics

et al. 2022

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The design and development of new phosphorus-containing amino acids and peptidomimetics have been attracting considerable attention due to their value as intermediates in the synthesis of biologically active compounds and the prospects for further pharmacological applications. 1,3-Oxazole derivatives, as masked peptides, constitute an important group of amino acid precursors that are widely used in contemporary organic synthesis. This review presents the 1,3-oxazole-based synthetic strategies of phosphorylated amino acids and peptides that have been published in both journal and patent literature. We have focused specifically on the synthesis of 4-phosphorylated 1,3-oxazoles as precursors of phosphopeptide mimetics containing the peptide chain with a non-terminal phosphono group due to the growing interest in finding efficient methods for the synthesis of this little-studied class of compounds

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“…αβ‐Didehydro‐α‐amino acids, commonly known as dehydroamino acids (ΔXaa), belong to nonstandard amino acids occurring primarily in natural peptides produced by bacteria and fungi . Dehydroamino acids continuously attract attention in various areas, mainly in synthesis, as designed products or suitable substrates, including asymmetric hydrogenation as well as in the conformational studies . Dehydrophenylalanine (ΔPhe), although scarcely presented in natural compounds, is the most often studied dehydroamino acid .…”

Section: Introductionmentioning

confidence: 99%

Conformational preferences and synthesis of isomers Z and E of oxazole‐dehydrophenylalanine

et al. 2016

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Dehydrophenylalanine, ΔPhe, is the most commonly studied α,β-dehydroamino acid. In nature, further modifications of the α,β-dehydroamino acids were found, for example, replacement of the C-terminal amide group by oxazole ring. The conformational properties of oxazole-dehydrophenylalanine residue (ΔPhe-Ozl), both isomers Z and E, were investigated. To determine all possible conformations, theoretical calculations were performed using Ac-(Z/E)-ΔPhe-Ozl(4-Me) model compounds at M06-2X/6-31++G(d,p) level of theory. Ac-(Z/E)-ΔPhe-Ozl-4-COOEt compounds were synthesized and the conformational preferences of each isomer, Z and E, were investigated using FTIR and NMR-NOE in solutions of increasing polarity (CHCl3 , DMSO-d6). The solid-state low-temperature structures of Ac-(Z)-ΔPhe-Ozl-4-COOEt and its intermediate analog Ac-(Z)-ΔPhe-Ozn(4-OH)-4-COOEt were also determined. In a weakly polar environment, the ΔPhe-Ozl residue has a tendency to adopt the conformation β2 with the calculated φ and ψ angles of -127° and 0° for the isomer Z and -170° and 26° for the isomer E. The increase of environment polarity favors the helical conformation α and the beta-turn like conformation β, but the conformation β2 seems to be still accessible. The (E)-ΔPhe-Ozl residue can be obtained from the isomer Z in photoisomerization reaction. However, hydroxyl-oxazoline-dehydrophenylalanine ΔPhe-Ozn(4-OH) decomposes in such conditions. Alternatively, (E)-ΔPhe-NH2 can be applied as a substrate in the Hantzsch reaction. © 2016 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 283-294, 2016.

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Synthesis of phosphorylated dehydrotyrosine-containing tripeptides from 5-amino-2-aminoalkyl-1,3-oxazole-4-phosphonic acids derivatives

Cited by 3 publications

References 9 publications

Phosphonopeptides containing free phosphonic groups: recent advances

Phosphonopeptides containing free phosphonic groups: recent advances

1,3-Oxazoles as precursors of phosphorylated amino acids and peptidomimetics

Conformational preferences and synthesis of isomers Z and E of oxazole‐dehydrophenylalanine

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