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Literature DB >> 24976298

Solid-phase synthesis of peptoid-like oligomers containing diverse diketopiperazine units.

Abstract

Diketopiperazine (DKP) units are found in many bioactive small molecules. Here we report facile chemistry for incorporating diverse DKP units within peptoid and peptoid-like libraries made by solid-phase split and pool synthesis.

Entities: Chemical

Mesh：

Substances：

Year: 2014 PMID： 24976298 PMCID： PMC4148721 DOI： 10.1039/c4ob00829d

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

9 in total

1. Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery.

Authors: R A Houghten; C Pinilla; S E Blondelle; J R Appel; C T Dooley; J H Cuervo
Journal: Nature Date: 1991-11-07 Impact factor: 49.962

2. A new type of synthetic peptide library for identifying ligand-binding activity.

Authors: K S Lam; S E Salmon; E M Hersh; V J Hruby; W M Kazmierski; R J Knapp
Journal: Nature Date: 1991-11-07 Impact factor: 49.962

Review 3. 2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products.

Authors: Alan D Borthwick
Journal: Chem Rev Date: 2012-05-11 Impact factor: 60.622

4. Synthesis of functionalized, unsymmetrical 1,3,4,6-tetrasubstituted 2,5-diketopiperazines.

Authors: Marcus Tullberg; Morten Grøtli; Kristina Luthman
Journal: J Org Chem Date: 2007-01-05 Impact factor: 4.354

5. Microwave-assisted solid-phase synthesis of 2,5-diketopiperazines: solvent and resin dependence.

Authors: Marcus Tullberg; Kristina Luthman; Morten Grøtli
Journal: J Comb Chem Date: 2006 Nov-Dec

6. Incorporation of heterocycles into the backbone of peptoids to generate diverse peptoid-inspired one bead one compound libraries.

Authors: Animesh Aditya; Thomas Kodadek
Journal: ACS Comb Sci Date: 2012-02-21 Impact factor: 3.784

7. Synthesis and screening of stereochemically diverse combinatorial libraries of peptide tertiary amides.

Authors: Yu Gao; Thomas Kodadek
Journal: Chem Biol Date: 2013-03-21

8. Synthesis of libraries of peptidomimetic compounds containing a 2-oxopiperazine unit in the main chain.

Authors: Sujit Suwal; Thomas Kodadek
Journal: Org Biomol Chem Date: 2013-04-07 Impact factor: 3.876

9. A biomimetic polyketide-inspired approach to small-molecule ligand discovery.

Authors: Claudio Aquino; Mohosin Sarkar; Michael J Chalmers; Kimberly Mendes; Thomas Kodadek; Glenn C Micalizio
Journal: Nat Chem Date: 2011-11-20 Impact factor: 24.427

9 in total

8 in total

1. Solid-Phase Synthesis of β-Amino Ketones Via DNA-Compatible Organocatalytic Mannich Reactions.

Authors: Nam Tran-Hoang; Thomas Kodadek
Journal: ACS Comb Sci Date: 2018-01-24 Impact factor: 3.784

2. High affinity binding of conformationally constrained synthetic oligomers to an antigen-specific antibody: Discovery of a diagnostically useful synthetic ligand for murine Type 1 diabetes autoantibodies.

Authors: Todd M Doran; Yu Gao; Scott Simanski; Patrick McEnaney; Thomas Kodadek
Journal: Bioorg Med Chem Lett Date: 2015-05-27 Impact factor: 2.823

Solid-phase synthesis of peptoid-like oligomers containing diverse diketopiperazine units.

1. Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery.

2. A new type of synthetic peptide library for identifying ligand-binding activity.

Review 3. 2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products.

4. Synthesis of functionalized, unsymmetrical 1,3,4,6-tetrasubstituted 2,5-diketopiperazines.

5. Microwave-assisted solid-phase synthesis of 2,5-diketopiperazines: solvent and resin dependence.

6. Incorporation of heterocycles into the backbone of peptoids to generate diverse peptoid-inspired one bead one compound libraries.

7. Synthesis and screening of stereochemically diverse combinatorial libraries of peptide tertiary amides.

8. Synthesis of libraries of peptidomimetic compounds containing a 2-oxopiperazine unit in the main chain.

9. A biomimetic polyketide-inspired approach to small-molecule ligand discovery.

1. Solid-Phase Synthesis of β-Amino Ketones Via DNA-Compatible Organocatalytic Mannich Reactions.

2. High affinity binding of conformationally constrained synthetic oligomers to an antigen-specific antibody: Discovery of a diagnostically useful synthetic ligand for murine Type 1 diabetes autoantibodies.

3. Expanding the known structure space for RNA binding: a test of 2,5-diketopiperazine.

4. Towards vast libraries of scaffold-diverse, conformationally constrained oligomers.

Review 5. Chemical Tools To Monitor and Manipulate Adaptive Immune Responses.

6. Rapid lead discovery through iterative screening of one bead one compound libraries.

7. Novel C6-substituted 1,3,4-oxadiazinones as potential anti-cancer agents.

8. Solid-Phase Insertion of N-mercaptoalkylglycine Residues into Peptides.