Buschhaus B, Bauer W, Hirsch A (2003)
Publication Type: Journal article, Original article
Publication year: 2003
Original Authors: Buschhaus B., Bauer W., Hirsch A.
Publisher: Elsevier
Book Volume: 59
Pages Range: 3899-3915
Journal Issue: 22
DOI: 10.1016/S0040-4020(03)00459-9
A new type of chiral depsipeptide dendrons based on tartaric acid as branching juncture and ω-aminocapronic acid as spacer has been prepared. Natural and unnatural tartaric acid building blocks have been incorporated, providing access to combinatorial libraries. All compounds have been completely characterized by FAB-MS, EA analysis, H/C NMR- and UV/Vis-spectroscopy. H NMR relaxation measurements have been used to examine the conformational flexibility of these dendrons in CHCN and CHOH and indicate a less flexible structure in CHCN. Pulse gradient spin echo (PGSE) NMR measurements correlate these findings to molecular dimensions. A reduced size for the dendrons in CHCN compared to CHOH leads to the assumption of a more compact structure in this solvent. Additional polarimetric data reveal, that observed changes in optical activity with increasing generation can in CHOH be explained by constitutional effects of the dendron structure but not in CHCN. CD measurements are in agreement with these findings and show a linear increase of the Cotton effects with increasing generation for CHOH but not for CHCN. It can be concluded that the conformation within the dendrons is very sensitive to environmental conditions and that a chiral secondary structure might be stabilized in CHCN. Initial studies revealed that chirality transfer to the focal functionality occurs. © 2003 Elsevier Science Ltd. All rights reserved.
APA:
Buschhaus, B., Bauer, W., & Hirsch, A. (2003). Synthesis and chiroptical properties of a new type of chiral depsipeptide dendrons. Tetrahedron, 59(22), 3899-3915. https://dx.doi.org/10.1016/S0040-4020(03)00459-9
MLA:
Buschhaus, Boris, Walter Bauer, and Andreas Hirsch. "Synthesis and chiroptical properties of a new type of chiral depsipeptide dendrons." Tetrahedron 59.22 (2003): 3899-3915.
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