Chemoselective Glycosylation of Peptides through S-Alkylation Reaction
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Chemoselective Glycosylation of Peptides through S-Alkylation Reaction (820 views) (PDF public 185 views)

Calce E, Digilio G, Menchise V, Saviano M, De Luca S

Chemistry (ISSN: 1521-3765electronic, 0947-6539linking), 2018 Apr 20; 24(23): 6231-6238.

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Paper type: Journal Article

Impact factor: 5.476, 5-year impact factor: 5.477

Url: http://www.chemistryviews.org/details/ezine/11014914/Efficient_Synthesis_of_S-Linked_Glycopeptides.html

Keywords: S-Alkylation, Chemoselective Method, Glycopeptide, Glycosil Halide, Post-Synthetic Modification, Chemistry, Glycosylation, Molecular Structure, Chemoselectivity, Glycosyl Halide, Peptide Modifications

Affiliations:
*** IBB - CNR ***

Institute di Biostructure and Bioimaging IBB-CNR, Via Mezzocannone 16, 80134, Naples, ITALY., Bari, 70126, Bari, ITALY.,
Institute of Biostructures and Bioimaging, National Research Council, 80134, Naples, Italy., Department of Science and Technologic Innovation, Universita del Piemonte Orientale "A. Avogadro", 15121, Alessandria, Italy., Institute of Biostructures and Bioimaging, National Research Council, c/o Molecular Biotechnology Center, 10126, Turin, Italy., Institute of Crystallography, National Research Council, 70126, Bari, Italy.,


References:
Not available.
Chemoselective Glycosylation of Peptides through S-Alkylation Reaction

An efficient and fast procedure in execution for synthesizing S-linked glycopeptides is reported. It uses activated molecular sieves as a base to promote the selective S-alkylation of readily prepared cysteine-containing peptides, upon reaction of appropriate glycosyl halides. Due to the very mild conditions employed, the chemoselective linkage of the electrophilic sugar with a peptide sulfhydryl group occurred in a satisfactory yield, allowing the incorporation of mono and disaccharide moieties. The sugar-peptide conjugates obtained from alpha-D-glycosyl derivatives adopt a beta-S-conformation, indicating the high stereoselectivity of the substitution reaction.
http://www.chemistryviews.org/details/ezine/11014914/Efficient_Synthesis_of_S-Linked_Glycopeptides.html
Chemoselective Glycosylation of Peptides through S-Alkylation Reaction

▼    Chemical modification of natural molecules, such as peptides and polysaccharides, to be employed as therapeutic agents as well as sensor diagnostic tools
Chemoselective Glycosylation of Peptides through S-Alkylation Reaction

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Verdoliva V, Digilio G, Saviano M, De Luca S
* Microwave Heating Promotes the S-Alkylation of Aziridine Catalyzed by Molecular Sieves: A Post-Synthetic Approach to Lanthionine-Containing Peptides (149 views)
Molecules (ISSN: 1420-3049linking, 1420-3049electronic), 2021 Oct 11; 26(20): 1-9.
Impact Factor: 4.411
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Canassa-deleo T, Campo VL, Rodrigues LC, Marchiori MF, Fuzo C, Brigido MM, Sandomenico A, Ruvo M, Maranhao AQ, Dias-baruffi M
* Multifaceted antibodies development against synthetic alpha-dystroglycan mucin glycopeptide as promising tools for dystroglycanopathies diagnostic (217 views)
Glycoconj J (ISSN: 0282-0080linking), 2020 Feb; 37(1): 77-93.
Impact Factor: 2.197
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De Luca S, Digilio G, Verdoliva V, Tovillas P, Jimenez-oses G, Peregrina JM
* Lanthionine Peptides by S-Alkylation with Substituted Cyclic Sulfamidates promoted by Activated Molecular Sieves: Effects of the Sulfamidate Structure on the Yield (289 views)
J Org Chem (ISSN: 0022-3263linking), 2019 Nov 15; 84(22): 14957-14964.
Impact Factor: 4.745
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De Luca S, Digilio G, Verdoliva V, Saviano M, Menchise V, Tovillas P, Jimenez-oses G, Peregrina JM
* A Late-Stage Synthetic Approach to Lanthionine-Containing Peptides via S-Alkylation on Cyclic Sulfamidates Promoted by Molecular Sieves (369 views)
Org Lett (ISSN: 1523-7052electronic, 1523-7052linking, 1523-7060), 2018 Nov 14; 20(23): 7478-7482.
Impact Factor: 6.492
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Leiria Campo V, Riul TB, Oliveira Bortot L, Martins-teixeira MB, Fiori Marchiori M, Iaccarino E, Ruvo M, Dias-baruffi M, Carvalho I
* A Synthetic MUC1 Glycopeptide Bearing betaGalNAc-Thr as a Tn Antigen Isomer Induces the Production of Antibodies against Tumor Cells (1571 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-4227linking), 2017 Mar 16; 18(6): 527-538.
Impact Factor: 2.774
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Calce E, De Luca S
Frontispiece: The Cysteine S-Alkylation Reaction as a Synthetic Method to Covalently Modify Peptide Sequences (9 views)
Chemistry A European Journal, 2017; 23 (2 ): 224-224.
Impact Factor:
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Calce E, De Luca S
The Cysteine S-Alkylation Reaction as a Synthetic Method to Covalently Modify Peptide Sequences (3 views)
Chemistry A European Journal, 2017; 23 (2 ): 224-233.
Impact Factor:
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Calce E, De Luca S
* The Cysteine S-Alkylation Reaction as a Synthetic Method to Covalently Modify Peptide Sequences (454 views)
Chemistry (ISSN: 0947-6539, 1521-3765, 1521-3765electronic), 2016 Aug 19; 22: 1-11.
Impact Factor: 5.317
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Calce E, De Luca S
* Microwave heating in peptide side chain modification via cysteine alkylation (372 views)
Amino Acids (ISSN: 0939-4451, 1438-2199, 1438-2199electronic), 2016 Jun 28; 48(9): 2267-2271.
Impact Factor: 3.173
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Calce E, Leone M, Mercurio FA, Monfregola L, De Luca S
* Solid-Phase S-Alkylation Promoted by Molecular Sieves (344 views)
Org Lett (ISSN: 1523-7060, 1523-7052, 1523-7052electronic), 2015 Nov 20; 17(22): 5646-5649.
Impact Factor: 6.732
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Comegna D, de Paola I, Saviano M, Del Gatto A, Zaccaro L
* Straightforward entry to s-glycosylated fmoc-amino acids and their application to solid phase synthesis of glycopeptides and glycopeptidomimetics (667 views)
Org Lett (ISSN: 1523-7060, 1523-7052, 1523-7052electronic), 2015; 17(3): 640-643.
Impact Factor: 6.732
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Calce E, Leone M, Monfregola L, De Luca S
* Chemical Modifications Of Peptide Sequences Via S-Alkylation Reaction (493 views)
Org Lett (ISSN: 1523-7060, 1523-7052, 1523-7052electronic), 2013; 15(20): 5354-5357.
Impact Factor: 6.324
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Saviano M, Improta R, Benedetti E, Carrozzini B, Cascarano GL, Didierjean C, Toniolo C, Crisma M
* Benzophenone photophore flexibility and proximity: Molecular and crystal-state structure of a Bpa-containing trichogin dodecapeptide analogue (487 views)
Chembiochem (ISSN: 1439-4227, 1439-7633, 1439-7633electronic), 2004 Apr 2; 5(4): 541-544.
Impact Factor: 3.474
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13 Records (13 excluding Abstracts).
Total impact factor: 52.371 (52.371 excluding Abstracts).
Total 5 year impact factor: 45.413 (45.413 excluding Abstracts).

Last modified by Marco Comerci on Tuesday 09 April 2024, 12:56:57
820 views. Last view on Saturday 14 September 2024, 21:06:36