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Literature DB >> 21738926

Sortase A-catalyzed peptide cyclization for the synthesis of macrocyclic peptides and glycopeptides.

Abstract

A chemoenzymatic method was developed for the synthesis of macrocyclic peptides and glycopeptides. Sortase A was found to mediate either head to tail cyclization or oligomerization and then head to tail cyclization of peptides and glycopeptides, depending on the peptide length, to produce 15-mer or higher cyclic peptides and glycopeptides.

Entities: Chemical Disease Species

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Year: 2011 PMID： 21738926 PMCID： PMC3174090 DOI： 10.1039/c1cc13322e

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

24 in total

Review 1. The cyclization of peptides and depsipeptides.

Authors: John S Davies
Journal: J Pept Sci Date: 2003-08 Impact factor: 1.905

2. Sortagging: a versatile method for protein labeling.

Authors: Maximilian W Popp; John M Antos; Gijsbert M Grotenbreg; Eric Spooner; Hidde L Ploegh
Journal: Nat Chem Biol Date: 2007-09-23 Impact factor: 15.040

3. Site-specific protein modification on living cells catalyzed by Sortase.

Authors: Tsutomu Tanaka; Teruyasu Yamamoto; Shinya Tsukiji; Teruyuki Nagamune
Journal: Chembiochem Date: 2008-03-25 Impact factor: 3.164

4. Expansion of the sortase-mediated labeling method for site-specific N-terminal labeling of cell surface proteins on living cells.

Authors: Teruyasu Yamamoto; Teruyuki Nagamune
Journal: Chem Commun (Camb) Date: 2009-01-07 Impact factor: 6.222

5. Macrocyclic peptidomimetics: potential for drug development.

Authors: R P McGeary; D P Fairlie
Journal: Curr Opin Drug Discov Devel Date: 1998-09

6. Sortase-catalyzed peptide-glycosylphosphatidylinositol analogue ligation.

Authors: Xueqing Guo; Qianli Wang; Benjamin M Swarts; Zhongwu Guo
Journal: J Am Chem Soc Date: 2009-07-29 Impact factor: 15.419

7. Synthesis of protein mimics with nonlinear backbone topology by a combined recombinant, enzymatic, and chemical synthesis strategy.

Authors: Stephan Pritz; Oliver Kraetke; Annerose Klose; Jana Klose; Sven Rothemund; Klaus Fechner; Michael Bienert; Michael Beyermann
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

8. Enhancement of sortase A-mediated protein ligation by inducing a β-hairpin structure around the ligation site.

Authors: Yuichi Yamamura; Hidehiko Hirakawa; Satoshi Yamaguchi; Teruyuki Nagamune
Journal: Chem Commun (Camb) Date: 2011-03-15 Impact factor: 6.222

9. Chemoenzymatic synthesis of glycosylphosphatidylinositol-anchored glycopeptides.

Authors: Zhimeng Wu; Xueqing Guo; Zhongwu Guo
Journal: Chem Commun (Camb) Date: 2010-06-24 Impact factor: 6.222

10. A new model for the presentation of tumor-associated antigens and the quest for an anticancer vaccine: a solution to the synthesis challenge via ring-closing metathesis.

Authors: Insik Jeon; Dongjoo Lee; Isaac J Krauss; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2009-10-14 Impact factor: 15.419

27 in total

Sortase A-catalyzed peptide cyclization for the synthesis of macrocyclic peptides and glycopeptides.

Review 1. The cyclization of peptides and depsipeptides.

2. Sortagging: a versatile method for protein labeling.

3. Site-specific protein modification on living cells catalyzed by Sortase.

4. Expansion of the sortase-mediated labeling method for site-specific N-terminal labeling of cell surface proteins on living cells.

5. Macrocyclic peptidomimetics: potential for drug development.

6. Sortase-catalyzed peptide-glycosylphosphatidylinositol analogue ligation.

7. Synthesis of protein mimics with nonlinear backbone topology by a combined recombinant, enzymatic, and chemical synthesis strategy.

8. Enhancement of sortase A-mediated protein ligation by inducing a β-hairpin structure around the ligation site.

9. Chemoenzymatic synthesis of glycosylphosphatidylinositol-anchored glycopeptides.

10. A new model for the presentation of tumor-associated antigens and the quest for an anticancer vaccine: a solution to the synthesis challenge via ring-closing metathesis.

Review 1. Enzymatic labeling of proteins: techniques and approaches.

2. Dynamic control of hydrogel crosslinking via sortase-mediated reversible transpeptidation.

3. Protein thioester synthesis enabled by sortase.

Review 4. Covalently circularized nanodiscs; challenges and applications.

5. Sortase-Mediated Transpeptidation for Site-Specific Modification of Peptides, Glycopeptides, and Proteins.

Review 6. Chemoenzymatic Methods for the Synthesis of Glycoproteins.

7. Semienzymatic cyclization of disulfide-rich peptides using Sortase A.

8. Site-specific C-terminal and internal loop labeling of proteins using sortase-mediated reactions.

9. The Catalytic Mechanism of the Marine-Derived Macrocyclase PatGmac.

Review 10. Mechanisms of cyanobactin biosynthesis.