Solid-Phase S-Alkylation Promoted by Molecular Sieves

被引：22

作者：

Calce, Enrica ^{[1
]}

Leone, Marilisa ^{[1
]}

Mercurio, Flavia Anna ^{[1
]}

Monfregola, Luca ^{[2
]}

De Luca, Stefania ^{[1
]}

机构：

[1] CNR, Inst Biostruct & Bioimaging, I-80134 Naples, Italy

[2] Univ Colorado, Dept Chem & Biochem, Boulder, CO 80309 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 22期

关键词：

CHEMICAL-MODIFICATION; LIPIDATED PEPTIDES; MEMBRANE;

D O I：

10.1021/acs.orglett.5b02931

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A solid-phase S-alkylation procedure to introduce chemical modification on the cysteine sulfhydryl group of a peptidyl resin is reported. The reaction is promoted by activated molecular sieves and consists of a solid-solid process, since both the catalyst and the substrate are in a solid state. The procedure was revealed to be efficient and versatile, particularly when used in combination with the solution S-alkylation approach, allowing for the introduction of different molecular diversities on the same peptide molecule.

引用

页码：5646 / 5649

页数：4

共 27 条

[1]

Albericio F., 2006, FMOC SOLID PHASE PEP

[2] Pyrene: A Probe to Study Protein Conformation and Conformational Changes [J].

Bains, Gursharan ;

Patel, Arti B. ;

Narayanaswami, Vasanthy .

MOLECULES, 2011, 16 (09) :7909-7935

[3] Protein Chemical Modification on Endogenous Amino Acids [J].

Basle, Emmanuel ;

Joubert, Nicolas ;

Pucheault, Mathieu .

CHEMISTRY & BIOLOGY, 2010, 17 (03) :213-227

[4]

BODANSZKY M, 1982, INT J PEPT PROT RES, V20, P434

[5] Air oxidation method employed for the disulfide bond formation of natural and synthetic peptides [J].

Calce, Enrica ;

Vitale, Rosa Maria ;

Scaloni, Andrea ;

Amodeo, Pietro ;

De Luca, Stefania .

AMINO ACIDS, 2015, 47 (08) :1507-1515

[6] Lipidated peptides via post-synthetic thioalkylation promoted by molecular sieves [J].

Calce, Enrica ;

Leone, Marilisa ;

Monfregola, Luca ;

De Luca, Stefania .

AMINO ACIDS, 2014, 46 (08) :1899-1905

[7] Chemical Modifications of Peptide Sequences via S-Alkylation Reaction [J].

Calce, Enrica ;

Leone, Marilisa ;

Monfregola, Luca ;

De Luca, Stefania .

ORGANIC LETTERS, 2013, 15 (20) :5354-5357

[8] Introduction to current and future protein therapeutics: A protein engineering perspective [J].

Carter, Paul J. .

EXPERIMENTAL CELL RESEARCH, 2011, 317 (09) :1261-1269

[9] Chemical Modification of Proteins at Cysteine: Opportunities in Chemistry and Biology [J].

Chalker, Justin M. ;

Bernardes, Goncalo J. L. ;

Lin, Yuya A. ;

Davis, Benjamin G. .

CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (05) :630-640

[10] Acid-Labile Cys-Protecting Groups for the Fmoc/tBu Strategy: Filling the Gap [J].

Gongora-Benitez, Miriam ;

Mendive-Tapia, Lorena ;

Ramos-Tomillero, Ivan ;

Breman, Arjen C. ;

Tulla-Puche, Judit ;

Albericio, Fernando .

ORGANIC LETTERS, 2012, 14 (21) :5472-5475

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