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Literature DB >> 14649893

Glycosyl phenylthiosulfonates (glyco-PTS): novel reagents for glycoprotein synthesis.

David P Gamblin¹, Philippe Garnier, Sarah J Ward, Neil J Oldham, Antony J Fairbanks, Benjamin G Davis.

Abstract

Controlled site-selective glycosylation can be achieved by combining site-directed cysteine mutagenesis with chemical modification of the introduced thiol; a new class of more efficient chemoselective reagents, glycosyl phenylthiosulfonates, allow rapid glycosylations of representative simple thiols, peptides and proteins.

Entities: Chemical

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Substances：

Year: 2003 PMID： 14649893 DOI： 10.1039/b306990g

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

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Cited

10 in total

Review 1. Thiol chemistry in peroxidase catalysis and redox signaling.

Authors: Alberto Bindoli; Jon M Fukuto; Henry Jay Forman
Journal: Antioxid Redox Signal Date: 2008-09 Impact factor: 8.401

2. Selective protein N-terminal labeling with N-hydroxysuccinimide esters.

Authors: Hanjie Jiang; Gabriel D D'Agostino; Philip A Cole; Daniel R Dempsey
Journal: Methods Enzymol Date: 2020-04-28 Impact factor: 1.600

3. Sigmatropic rearrangements as tools for amino acid and peptide modification: application of the allylic sulfur ylide rearrangement to the preparation of neoglycoconjugates and other conjugates.

Authors: David Crich; Yekui Zou; Franck Brebion
Journal: J Org Chem Date: 2006-11-24 Impact factor: 4.354

Review 4. Homo- and Heterogeneous Glycoconjugates on the Basis of N-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation.

Authors: Almira Kurbangalieva; Regina Zamalieva; Igor Nasibullin; Kenshiro Yamada; Katsunori Tanaka
Journal: Molecules Date: 2022-02-14 Impact factor: 4.411

5. Allylic selenosulfide rearrangement: a method for chemical ligation to cysteine and other thiols.

Authors: David Crich; Venkataramanan Krishnamurthy; Thomas K Hutton
Journal: J Am Chem Soc Date: 2006-03-01 Impact factor: 15.419

6. Dechalcogenative allylic selenosulfide and disulfide rearrangements: complementary methods for the formation of allylic sulfides in the absence of electrophiles. Scope, limitations, and application to the functionalization of unprotected peptides in aqueous media.

Authors: David Crich; Venkataramanan Krishnamurthy; Franck Brebion; Maheswaran Karatholuvhu; Venkataraman Subramanian; Thomas K Hutton
Journal: J Am Chem Soc Date: 2007-07-27 Impact factor: 15.419

Glycosyl phenylthiosulfonates (glyco-PTS): novel reagents for glycoprotein synthesis.

Review 1. Thiol chemistry in peroxidase catalysis and redox signaling.

2. Selective protein N-terminal labeling with N-hydroxysuccinimide esters.

3. Sigmatropic rearrangements as tools for amino acid and peptide modification: application of the allylic sulfur ylide rearrangement to the preparation of neoglycoconjugates and other conjugates.

Review 4. Homo- and Heterogeneous Glycoconjugates on the Basis of N-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation.

5. Allylic selenosulfide rearrangement: a method for chemical ligation to cysteine and other thiols.

6. Dechalcogenative allylic selenosulfide and disulfide rearrangements: complementary methods for the formation of allylic sulfides in the absence of electrophiles. Scope, limitations, and application to the functionalization of unprotected peptides in aqueous media.

7. Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides.

Review 8. Chemical modifications of proteins and their applications in metalloenzyme studies.

9. A straightforward and convenient synthesis of functionalized allyl thiosulfonates and allyl disulfanes.

10. Chemoenzymatic Fc glycosylation via engineered aldehyde tags.