<b>Transformation of Serine to Cysteine. β-Elimination Reactions in Serine Derivatives</b>

Photaki, Iphigenia

doi:10.1021/ja00891a019

Cited by 124 publications

(30 citation statements)

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“…Other methods involve the nucleophilic attack by cysteine derivatives on ␤-haloalanines, ␤-tosylated serine, and ␤-tosylated threonine. 38,[41][42][43][44][45] These syntheses proved problematic in solution because of difficult purifications, poor yields, and lack of stereochemical control. Dugave and Menez 46 avoided epimerization, a common side reaction, by using N-trityl-3-iodoalanine benzyl ester as a hindered electrophile and were able to synthesize Fmoc-protected lanthionines successfully.…”

Section: Design and Synthesis Of Target Peptidesmentioning

confidence: 99%

Incorporation of thioether building blocks into an α_vβ₃‐specific RGD peptide: Synthesis and biological activity

et al. 2003

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We report the design, synthesis, and binding affinities of a family of thioether analogues of the alpha(v)beta(3)-specific compound c[(Mpa)RGDD(tBuG)C]-NH(2). The synthesis of the thioether building blocks is scalable and produced the desired products in good yields. The linear peptides were synthesized on solid supports, followed by cyclization in solution. Our analogues demonstrate interesting binding data to the isolated receptors. In particular, the peptide c[NH-Arg-Gly-Asp-Asp-(tBuG)-Cys(S-CH(2)-CO)]NH(2) (1) exhibits differences in binding when compared to the parent compound and demonstrates potent affinity to the alpha(v)beta(3) and alpha(5)beta(1) receptors while having reduced binding to the alpha(IIb)beta(3) receptor. This result combined with the replacement of the disulfide with a thioether makes this compound interesting for further development.

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Section: Design and Synthesis Of Target Peptidesmentioning

confidence: 99%

Incorporation of thioether building blocks into an α_vβ₃‐specific RGD peptide: Synthesis and biological activity

et al. 2003

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“…The coupling conditions used in the PVam series formed the new amide bond; after removal of by-products, dehydrochlorination with Et3N in EtoAc proceeded smoothly affording monomer i_~0, which could be hydrolyzed in base (PHOTAKI, 1963) to give the dehydroalanine monomer Ii.…”

Section: P Oly(dehydroalanine) Analogsmentioning

confidence: 99%

Hydrophilic polymers containing chiral nucleic acid base pendants as polynucleotide analogs

et al. 1981

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A survey of our recent work on synthetic polynucleotide analogs is given.Propionic acid and 3-methyl butyric acid derivatives substituted in the 2-position with nucleic acid bases have been used as chiral pendants for attachment to hydrophilic polyamine backbones. Hindered rotation about the amide bonds formed promotes a base-stacked structure as shown by ultraviolet hypochromic effects versus model compounds.If the pendant has been resolved, an optically active polymer results which may be studied by circular dichroism (CD).Thus, poly(ethylenimine) containing the (-)-2-(thymin-l-yl)propionyl group as the grafted pendant showed exciton coupling of the B2u transition of the base chromophores in the CD, as observed in polynucleotides. This implies at least a local helical order in the stacking.The biological activity of such structures is briefly discussed.

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“…A point of interest in the characterization of I1 was the absence of a nitrile absorption band at 4.4-4.5 p. The occasional marked diminution or absence of this band in certain oxygen-rich compounds has been noted previously (47). Subsequent attempts were unsuccessful in displacing the tosyl group of 111 by treatment with thioacetate (as with serine conversion to cysteine (48,49)), or with thiobenzoate (as reported for the thiobenzoylation of N-O-ditosyl-4-HypOCH3 (50)).…”

Section: N-acetyl-o-tosyl-4-hydroxy-~-proline Amide N-mentioning

confidence: 99%

Synthesis of Peptides and Derivatives of 3‐ and 4‐ Hydroxyproline

Adams

1976

International Journal of Peptide and Protein Research

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Synthesis and properties are reported for a number of peptides and related derivatives of 3‐hydroxy‐L‐proline and 4‐hydroxy‐L‐proline. These were made for several different purposes, namely, synthesis of N‐acetyl‐O‐tosyl‐4‐hydroxy‐L‐proline amide as a model for chemical reduction of peptide‐bound hydroxyproline, synthesis of tripeptides with the sequence glycyl‐4‐hydroxy‐L‐prolyl‐X, synthesis of the naturally occurring sequence, glycyl‐3‐hydroxy‐L‐prolyl‐4‐hydroxy‐L‐proline, and monomers for polymerization to yield the sequence ‐glycyl‐prolyl‐4‐hydroxy‐L‐prolyl‐.

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Transformation of Serine to Cysteine. β-Elimination Reactions in Serine Derivatives

Cited by 124 publications

References 0 publications

Incorporation of thioether building blocks into an α_vβ₃‐specific RGD peptide: Synthesis and biological activity

Incorporation of thioether building blocks into an α_vβ₃‐specific RGD peptide: Synthesis and biological activity

Hydrophilic polymers containing chiral nucleic acid base pendants as polynucleotide analogs

Synthesis of Peptides and Derivatives of 3‐ and 4‐ Hydroxyproline

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Transformation of Serine to Cysteine. β-Elimination Reactions in Serine Derivatives

Cited by 124 publications

References 0 publications

Incorporation of thioether building blocks into an αvβ3‐specific RGD peptide: Synthesis and biological activity

Incorporation of thioether building blocks into an αvβ3‐specific RGD peptide: Synthesis and biological activity

Hydrophilic polymers containing chiral nucleic acid base pendants as polynucleotide analogs

Synthesis of Peptides and Derivatives of 3‐ and 4‐ Hydroxyproline

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Product

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Incorporation of thioether building blocks into an α_vβ₃‐specific RGD peptide: Synthesis and biological activity

Incorporation of thioether building blocks into an α_vβ₃‐specific RGD peptide: Synthesis and biological activity