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Literature DB >> 23210770

Substituted imidazo[1,2-a]pyridines as β-strand peptidomimetics.

Chang Won Kang¹, Yongmao Sun, Juan R Del Valle.

Abstract

New conformationally extended dipeptide surrogates based on an imidazo[1,2-a]pyridine scaffold are described. Efficient synthesis and incorporation into host peptides affords structures with native side-chain functionality and hydrogen bonding elements on one face of the backbone. Structural analysis by NMR suggests that model peptidomimetics adopt a β-strand-like conformation in solution.

Entities: Chemical Disease Gene Species

Mesh：

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Year: 2012 PMID： 23210770 PMCID： PMC3528799 DOI： 10.1021/ol302850n

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

35 in total

Review 1. Conformational homogeneity in molecular recognition by proteolytic enzymes.

Authors: J D Tyndall; D P Fairlie
Journal: J Mol Recognit Date: 1999 Nov-Dec Impact factor: 2.137

2. Probing the hydrophobic pocket of farnesyltransferase: aromatic substitution of CAAX peptidomimetics leads to highly potent inhibitors.

Authors: Y Qian; J J Marugan; R D Fossum; A Vogt; S M Sebti; A D Hamilton
Journal: Bioorg Med Chem Date: 1999-12 Impact factor: 3.641

3. A 1,3-phenyl-linked hydantoin oligomer scaffold as a β-strand mimetic.

Authors: Andrew G Jamieson; David Russell; Andrew D Hamilton
Journal: Chem Commun (Camb) Date: 2012-03-07 Impact factor: 6.222

Review 4. Update 1 of: Beta-strand mimetics.

Authors: Wendy A Loughlin; Joel D A Tyndall; Matthew P Glenn; Timothy A Hill; David P Fairlie
Journal: Chem Rev Date: 2010-04-12 Impact factor: 60.622

5. Synthesis of GSK3β mimetic inhibitors of Akt featuring a novel extended dipeptide surrogate.

Authors: Sujeewa Ranatunga; Juan R Del Valle
Journal: Bioorg Med Chem Lett Date: 2011-09-28 Impact factor: 2.823

6. Universal peptidomimetics.

Authors: Eunhwa Ko; Jing Liu; Lisa M Perez; Genliang Lu; Amber Schaefer; Kevin Burgess
Journal: J Am Chem Soc Date: 2010-12-23 Impact factor: 15.419

7. Structure guided development of novel thymidine mimetics targeting Pseudomonas aeruginosa thymidylate kinase: from hit to lead generation.

Authors: Jun Yong Choi; Mark S Plummer; Jeremy Starr; Charlene R Desbonnet; Holly Soutter; Jeanne Chang; J Richard Miller; Keith Dillman; Alita A Miller; William R Roush
Journal: J Med Chem Date: 2012-01-13 Impact factor: 7.446

8. Reaction of β-lactam carbenes with 2-pyridyl isonitriles: a one-pot synthesis of 2-carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines useful as fluorescent probes for mercury ion.

Authors: Na Shao; Guang-Xian Pang; Cai-Xia Yan; Gao-Feng Shi; Ying Cheng
Journal: J Org Chem Date: 2011-08-24 Impact factor: 4.354

9. The basis for K-Ras4B binding specificity to protein farnesyltransferase revealed by 2 A resolution ternary complex structures.

Authors: S B Long; P J Casey; L S Beese
Journal: Structure Date: 2000-02-15 Impact factor: 5.006

Substituted imidazo[1,2-a]pyridines as β-strand peptidomimetics.

Review 1. Conformational homogeneity in molecular recognition by proteolytic enzymes.

2. Probing the hydrophobic pocket of farnesyltransferase: aromatic substitution of CAAX peptidomimetics leads to highly potent inhibitors.

3. A 1,3-phenyl-linked hydantoin oligomer scaffold as a β-strand mimetic.

Review 4. Update 1 of: Beta-strand mimetics.

5. Synthesis of GSK3β mimetic inhibitors of Akt featuring a novel extended dipeptide surrogate.

6. Universal peptidomimetics.

7. Structure guided development of novel thymidine mimetics targeting Pseudomonas aeruginosa thymidylate kinase: from hit to lead generation.

8. Reaction of β-lactam carbenes with 2-pyridyl isonitriles: a one-pot synthesis of 2-carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines useful as fluorescent probes for mercury ion.

9. The basis for K-Ras4B binding specificity to protein farnesyltransferase revealed by 2 A resolution ternary complex structures.

10. Pyrrolinone-pyrrolidine oligomers as universal peptidomimetics.

Review 1. Systematic Targeting of Protein-Protein Interactions.

2. Imidazo[1,2-a]pyridine-based peptidomimetics as inhibitors of Akt.

3. Covalent and Noncovalent Targeting of the Tcf4/β-Catenin Strand Interface with β-Hairpin Mimics.

4. Anatomy of β-strands at protein-protein interfaces.