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Literature DB >> 12423081

Peptide-small molecule hybrids via orthogonal deprotection-chemoselective conjugation to cysteine-anchored scaffolds. A model study.

Amos B Smith¹, Sergey N Savinov, Uma V Manjappara, Irwin M Chaiken.

Abstract

The feasibility of an orthogonal deprotection-conjugation protocol, holding the promise of libraries of functionally diverse chemical probes attached to cysteine-anchored peptide scaffolds, has been explored with a model system. The necessary tools for assembly of the hybrid libraries have been prepared and the tandem procedure optimized. S-alkylation and S-sulfenylation are featured as the chemoselective ligation reactions. [reaction: see text]

Entities: Chemical

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Year: 2002 PMID： 12423081 DOI： 10.1021/ol026736d

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

9 in total

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2. Structure-activity relationships in the binding of chemically derivatized CD4 to gp120 from human immunodeficiency virus.

Authors: Hui Xie; Danny Ng; Sergey N Savinov; Barna Dey; Peter D Kwong; Richard Wyatt; Amos B Smith; Wayne A Hendrickson
Journal: J Med Chem Date: 2007-09-06 Impact factor: 7.446

3. N-methylcysteine-mediated total chemical synthesis of ubiquitin thioester.

Authors: Lesly A Erlich; K S Ajish Kumar; Mahmood Haj-Yahya; Philip E Dawson; Ashraf Brik
Journal: Org Biomol Chem Date: 2010-03-11 Impact factor: 3.876

4. Structural determinants for affinity enhancement of a dual antagonist peptide entry inhibitor of human immunodeficiency virus type-1.

Authors: Hosahudya Gopi; M Umashankara; Vanessa Pirrone; Judith LaLonde; Navid Madani; Ferit Tuzer; Sabine Baxter; Isaac Zentner; Simon Cocklin; Navneet Jawanda; Shendra R Miller; Arne Schön; Jeffrey C Klein; Ernesto Freire; Fred C Krebs; Amos B Smith; Joseph Sodroski; Irwin Chaiken
Journal: J Med Chem Date: 2008-04-11 Impact factor: 7.446

Peptide-small molecule hybrids via orthogonal deprotection-chemoselective conjugation to cysteine-anchored scaffolds. A model study.

1. Chemically ubiquitylated histone H2B stimulates hDot1L-mediated intranucleosomal methylation.

2. Structure-activity relationships in the binding of chemically derivatized CD4 to gp120 from human immunodeficiency virus.

3. N-methylcysteine-mediated total chemical synthesis of ubiquitin thioester.

4. Structural determinants for affinity enhancement of a dual antagonist peptide entry inhibitor of human immunodeficiency virus type-1.

Review 5. Hydrogen sulfide (H2S) releasing agents: chemistry and biological applications.

6. Light-Mediated Sulfenic Acid Generation from Photocaged Cysteine Sulfoxide.

7. Total chemical synthesis of histones and their analogs, assisted by native chemical ligation and palladium complexes.

8. Photo-cleavable purification/protection handle assisted synthesis of giant modified proteins with tandem repeats.

9. Mechanistic studies on the substrate-tolerant lanthipeptide synthetase ProcM.