This subproject is one of many research subprojects utilizing the resources provided by a Center grant funded by NIH/NCRR. The subproject and investigator (PI) may have received primary funding from another NIH source, and thus could be represented in other CRISP entries. The institution listed is for the Center, which is not necessarily the institution for the investigator. Project III: Fox The aim of this research program is to develop stereo- and enantioselective methods for using cyclopropenes and bicyclobutanes to prepare small ring analogs amino acids. Cyclopropyl and cyclobutyl amino acids have important biomedical applications and should find application in protein design. However, the existing synthetic methods give access to a limited range of functional groups and substitution patterns. The new approach is of significance to national interests in the health related sciences because the current state of the art does not permit small ring amino acids to be prepared easily or in variety. Accordingly, the specific aims of this proposal are to develop the following: (1) general methods for the Cu-catalyzed carbometallation reactions of cyclopropenes that proceed with either syn or anti selectivity. (2) procedures that convert the cyclopropyl anions from Aim 1 to cyclopropyl amines. (3) methodology that permits the incorporation of biologically relevant functional groups into these scaffolds. (4) an enantioselective deprotonation route for the asymmetric synthesis of cyclopropenes. (5) an enantioselective version of (1) and application to the synthesis and cyclopropyl amino acids. (6) protocols that convert enantiomerically enriched cyclopropenes to bicyclobutanes, and subsequently to cyclobutane amino acid derivatives.

Agency
National Institute of Health (NIH)
Institute
National Center for Research Resources (NCRR)
Type
Exploratory Grants (P20)
Project #
5P20RR017716-05
Application #
7381974
Study Section
Special Emphasis Panel (ZRR1-RI-A (03))
Project Start
2006-07-01
Project End
2007-06-30
Budget Start
2006-07-01
Budget End
2007-06-30
Support Year
5
Fiscal Year
2006
Total Cost
$181,810
Indirect Cost
Name
University of Delaware
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
059007500
City
Newark
State
DE
Country
United States
Zip Code
19716
Li, Linqing; Stiadle, Jeanna M; Levendoski, Elizabeth E et al. (2018) Biocompatibility of injectable resilin-based hydrogels. J Biomed Mater Res A 106:2229-2242
Drolen, Claire; Conklin, Eric; Hetterich, Stephen J et al. (2018) pH-Driven Mechanistic Switching from Electron Transfer to Energy Transfer between [Ru(bpy)3]2+ and Ferrocene Derivatives. J Am Chem Soc 140:10169-10178
Potocny, Andrea M; Riley, Rachel S; O'Sullivan, Rachel K et al. (2018) Photochemotherapeutic Properties of a Linear Tetrapyrrole Palladium(II) Complex displaying an Exceptionally High Phototoxicity Index. Inorg Chem 57:10608-10615
Potocny, Andrea M; Pistner, Allen J; Yap, Glenn P A et al. (2017) Electrochemical, Spectroscopic, and 1O2 Sensitization Characteristics of Synthetically Accessible Linear Tetrapyrrole Complexes of Palladium and Platinum. Inorg Chem 56:12703-12711
Li, Linqing; Stiadle, Jeanna M; Lau, Hang K et al. (2016) Tissue engineering-based therapeutic strategies for vocal fold repair and regeneration. Biomaterials 108:91-110
Li, Linqing; Mahara, Atsushi; Tong, Zhixiang et al. (2016) Recombinant Resilin-Based Bioelastomers for Regenerative Medicine Applications. Adv Healthc Mater 5:266-75
Ooms, Kristopher J; Vega, Alexander J; Polenova, Tatyana et al. (2015) Double and zero quantum filtered (2)H NMR analysis of D2O in intervertebral disc tissue. J Magn Reson 258:6-11
Suiter, Christopher L; Quinn, Caitlin M; Lu, Manman et al. (2015) MAS NMR of HIV-1 protein assemblies. J Magn Reson 253:10-22
Li, Linqing; Luo, Tianzhi; Kiick, Kristi L (2015) Temperature-triggered phase separation of a hydrophilic resilin-like polypeptide. Macromol Rapid Commun 36:90-5
Lau, Hang Kuen; Kiick, Kristi L (2015) Opportunities for multicomponent hybrid hydrogels in biomedical applications. Biomacromolecules 16:28-42

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