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Literature DB >> 21892506

Acyl hydrazides as peptoid sub-monomers.

Bani Kanta Sarma¹, Muhammed Yousufuddin, Thomas Kodadek.

Abstract

The use of acyl hydrazides as peptoid sub-monomers is investigated. We demonstrate here that azapeptoids derived entirely from acyl hydrazides can be made conveniently and efficiently using standard peptoid sub-monomer chemistry. Structural studies reveal that the main chain amide bond in these molecules predominantly adopts a trans conformation. A high-quality one bead one compound library of tetramers was made by split and pool synthesis and we found that the identity of the molecule on a single bead could be determined by tandem MALDI mass spectrometry. This journal is © The Royal Society of Chemistry 2011

Entities: Chemical Gene Species

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Year: 2011 PMID： 21892506 PMCID： PMC3882750 DOI： 10.1039/c1cc12750k

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

23 in total

1. Submonomer Solution Synthesis of Hydrazinoazapeptoids, a New Class of Pseudopeptides.

Authors: Arnaud Cheguillaume; Françoise Lehardy; Karine Bouget; Michèle Baudy-Floc'h; Philippe Le Grel
Journal: J Org Chem Date: 1999-04-16 Impact factor: 4.354

2. Construction of peptoids with all trans-amide backbones and peptoid reverse turns via the tactical incorporation of N-aryl side chains capable of hydrogen bonding.

Authors: Joseph R Stringer; J Aaron Crapster; Ilia A Guzei; Helen E Blackwell
Journal: J Org Chem Date: 2010-09-17 Impact factor: 4.354

3. 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

4. General method for rapid synthesis of multicomponent peptide mixtures.

Authors: A Furka; F Sebestyén; M Asgedom; G Dibó
Journal: Int J Pept Protein Res Date: 1991-06

5. Novel pyrrolopyrimidine-based α-helix mimetics: cell-permeable inhibitors of protein−protein interactions.

Authors: Ji Hoon Lee; Qi Zhang; Sunhwan Jo; Sergio C Chai; Misook Oh; Wonpil Im; Hua Lu; Hyun-Suk Lim
Journal: J Am Chem Soc Date: 2011-02-02 Impact factor: 15.419

6. Retro hydrazino-azapeptoids as peptidomimetics of proteasome inhibitors.

Authors: Sandrine Aubin; Bénédicte Martin; Jean-Guy Delcros; Yannick Arlot-Bonnemains; Michèle Baudy-Floc'h
Journal: J Med Chem Date: 2005-01-13 Impact factor: 7.446

7. Sequence-specific polypeptoids: a diverse family of heteropolymers with stable secondary structure.

Authors: K Kirshenbaum; A E Barron; R A Goldsmith; P Armand; E K Bradley; K T Truong; K A Dill; F E Cohen; R N Zuckermann
Journal: Proc Natl Acad Sci U S A Date: 1998-04-14 Impact factor: 11.205

8. Oligo(N-aryl glycines): a new twist on structured peptoids.

Authors: Neel H Shah; Glenn L Butterfoss; Khanh Nguyen; Barney Yoo; Richard Bonneau; Dallas L Rabenstein; Kent Kirshenbaum
Journal: J Am Chem Soc Date: 2008-12-10 Impact factor: 15.419

9. Conformational rearrangements by water-soluble peptoid foldamers.

Authors: Sung Bin Y Shin; Kent Kirshenbaum
Journal: Org Lett Date: 2007-10-26 Impact factor: 6.005

10. Structural and spectroscopic studies of peptoid oligomers with alpha-chiral aliphatic side chains.

Authors: Cindy W Wu; Kent Kirshenbaum; Tracy J Sanborn; James A Patch; Kai Huang; Ken A Dill; Ronald N Zuckermann; Annelise E Barron
Journal: J Am Chem Soc Date: 2003-11-05 Impact factor: 15.419

16 in total

1. Identification of selective covalent inhibitors of platelet activating factor acetylhydrolase 1B2 from the screening of an oxadiazolone-capped peptoid-azapeptoid hybrid library.

Authors: Bani Kanta Sarma; Xiaodan Liu; Thomas Kodadek
Journal: Bioorg Med Chem Date: 2016-04-23 Impact factor: 3.641

Acyl hydrazides as peptoid sub-monomers.

1. Submonomer Solution Synthesis of Hydrazinoazapeptoids, a New Class of Pseudopeptides.

2. Construction of peptoids with all trans-amide backbones and peptoid reverse turns via the tactical incorporation of N-aryl side chains capable of hydrogen bonding.

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

4. General method for rapid synthesis of multicomponent peptide mixtures.

5. Novel pyrrolopyrimidine-based α-helix mimetics: cell-permeable inhibitors of protein−protein interactions.

6. Retro hydrazino-azapeptoids as peptidomimetics of proteasome inhibitors.

7. Sequence-specific polypeptoids: a diverse family of heteropolymers with stable secondary structure.

8. Oligo(N-aryl glycines): a new twist on structured peptoids.

9. Conformational rearrangements by water-soluble peptoid foldamers.

10. Structural and spectroscopic studies of peptoid oligomers with alpha-chiral aliphatic side chains.

1. Identification of selective covalent inhibitors of platelet activating factor acetylhydrolase 1B2 from the screening of an oxadiazolone-capped peptoid-azapeptoid hybrid library.

Review 2. Chemical tools to monitor and manipulate the adaptive immune system.

3. Solid phase synthesis of 1,3,4-oxadiazin-5 (6R)-one and 1,3,4-oxadiazol-2-one scaffolds from acyl hydrazides.

4. First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation.

5. Rapid development of a potent photo-triggered inhibitor of the serine hydrolase RBBP9.

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

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

8. Submonomer synthesis of a hybrid peptoid-azapeptoid library.

9. A liquid array platform for the multiplexed analysis of synthetic molecule-protein interactions.

10. Submonomer synthesis of peptoids containing trans-inducing N-imino- and N-alkylamino-glycines.