An improved, scalable synthesis of bis-amino acids

TETRAHEDRON LETTERS

卷:57

Article

Cheong, Jae Eun¹  Pfeiffer, Conrad T.¹  Northrup, Justin D.¹  Parker, Matthew F. L.²  Schafmeister, Christian E.¹ 

[1] Temple Univ, Dept Chem, 1901 N 13th St, Philadelphia, PA 19122 USA

[2] Univ Calif San Francisco, Dept Radiol & Biomed Imaging, San Francisco, CA 94143 USA

关键词: Spiroligomer;    Bis-amino acids;    Amino acids;    Peptidomimetics;    Diastereomers;   

DOI  :  10.1016/j.tetlet.2016.09.032

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

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