Journal
TETRAHEDRON LETTERS
Volume 57, Issue 44, Pages 4882-4884Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.09.032
Keywords
Spiroligomer; Bis-amino acids; Amino acids; Peptidomimetics; Diastereomers
Categories
Funding
- National Science Foundation [1300231]
- NIH/NIGMS [GM067866]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1300231] Funding Source: National Science Foundation
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trans-4-Hydroxy-L-proline derived bis-amino acids are chiral, cyclic building blocks that display two alpha-amino acids that are differentiated from each other with protecting groups. They are assembled into spiroligomers-rigid, shape-programmable spirocyclic oligomers that are both stereochemically and functionally diverse. The synthesis presented here focuses on recent improvements that allow for a convenient, large-scale synthesis of twelve stereochemically pure bis-amino acids from inexpensive trans-4-hydroxy-L-proline. The bis-amino acids differ in stereochemistry as well as the amine protecting group, one of which (para-nitrobenzyl carbamate) has not been previously incorporated into bis-amino acids. (C) 2016 Elsevier Ltd. All rights reserved.
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