Thumbnail Image
Item

Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers

Xie, Yihui
; 
Luo, Danni
; 
Wiener, Jesse
; 
Tang, Sicheng
; 
Chepyshev, Sergiy
; 
Schafmeister, Christian
Citations
Altmetric:
Genre
Journal article
Date
2022-05-02
Advisor
Committee member
Group
Department
Chemistry
Subject
Amines
 Functional groups
 Functionalization
 Molecular structure
 Solid phase synthesis
Permanent link to this record
http://hdl.handle.net/20.500.12613/10466
 http://dx.doi.org/10.34944/dspace/10428
Collections
Faculty/Researcher Works
Show all metadata
Files
Thumbnail Image
XieEtAl-JournalArticle-2022-05.pdf
Adobe PDF, 1.01 MB
Research Projects
Organizational Units
Journal Issue
DOI
http://dx.doi.org/10.1021/acs.orglett.2c01295
Abstract
We report the fluorenylmethoxycarbonyl (Fmoc) protection of functionalized bis-amino acid building blocks using a temporary Cu2+ complexation strategy, together with an efficient multikilogram-scale synthesis of bis-amino acid precursors. This allows the synthesis of stereochemically and functionally diverse spiroligomers utilizing solid-phase Fmoc/tBu chemistry to facilitate the development of applications. Four tetramers were assembled on a semiautomated microwave peptide synthesizer. We determined their secondary structures with two-dimensional nuclear magnetic resonance spectroscopy.
Description
Citation
Development of Fmoc-Protected Bis-Amino Acids toward Automated Synthesis of Highly Functionalized Spiroligomers Yihui Xie, Danni Luo, Jesse Wiener, Sicheng Tang, Sergiy Chepyshev, and Christian Schafmeister Organic Letters 2022 24 (18), 3421-3425 DOI: 10.1021/acs.orglett.2c01295
Citation to related work
American Chemical Society (ACS)
Has part
Organic Letters, Vol. 24, Iss. 18
ADA compliance
For Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu
Embedded videos