Synthesis of aromatic bis- and tris(amino acids) and chiral dendrimers
(1999)- Abstract
- A number of protected aromatic bis- and tris(amino acids) have been synthesised by catalytic asymmetric hydrogenation of the corresponding didehydroamino acid derivatives. The didehydroamino acid derivatives were prepared either by a Heck coupling of a 2-amidoacrylate with an aryl dihalide, or by Horner-Wadsworth-Emmons olefination of aromatic aldehydes with phosphonylglycine reagents. Excellent stereochemical purity could be achieved in most cases.
The bis- and tris(amino acids) were then used as building blocks in a model study, the purpose of which was to assess the feasibility of constructing synthetic receptors from tris(amino acids). Several macrocyclic peptide-like compounds were prepared.
... (More) - A number of protected aromatic bis- and tris(amino acids) have been synthesised by catalytic asymmetric hydrogenation of the corresponding didehydroamino acid derivatives. The didehydroamino acid derivatives were prepared either by a Heck coupling of a 2-amidoacrylate with an aryl dihalide, or by Horner-Wadsworth-Emmons olefination of aromatic aldehydes with phosphonylglycine reagents. Excellent stereochemical purity could be achieved in most cases.
The bis- and tris(amino acids) were then used as building blocks in a model study, the purpose of which was to assess the feasibility of constructing synthetic receptors from tris(amino acids). Several macrocyclic peptide-like compounds were prepared.
Chiral dendrimers were also synthesised from the bis- and tris(amino acids). These dendrimers could be deprotected to yield water-soluble, polycationic or polyanionic macromolecules with a common structure. A chiroptical study of the protected dendrimers was undertaken, and it indicated that the solution shape is rather flat and sterically uncongested. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/40186
- author
- Ritzén, Andreas LU
- supervisor
- opponent
-
- Prof Liskamp, Rob. M. J., Utrecht University, The Netherlands
- organization
- publishing date
- 1999
- type
- Thesis
- publication status
- published
- subject
- keywords
- Organisk kemi, Organic chemistry, HWE reaction, asymmetric hydrogenation, Heck reaction, Amino acids, chiral dendrimers
- pages
- 66 pages
- publisher
- Department of Organic Chemistry, Lund University
- defense location
- Center for Chemistry and Chemical Engineering
- defense date
- 2000-01-21 10:15:00
- external identifiers
-
- other:ISRN: LUNDL/NKOK-1041-SE
- language
- English
- LU publication?
- yes
- additional info
- Article: (I) Basu, B.; Chattopadhyay, S. K.; Ritzén, A.; Frejd, T. Synthesis of optically active 1,1’-ferrocenylene-bis-alanine carrying four different protecting groups Tetrahedron: Asymmetry 1997, 8, 1841-1846. Article: (II) Ritzén, A.; Basu, B.; Chattopadhyay, S. K.; Dossa, F.; Frejd, T. Synthesis of optically active arylene bis-alanine derivatives carrying orthogonal protecting groups Tetrahedron: Asymmetry 1998, 9, 503-512. Article: (III) Ritzén, A.; Basu, B.; Wållberg, A.; Frejd, T. Phenyltrisalanine: a new, C3-symmetric, trifunctional amino acid Tetrahedron: Asymmetry 1998, 9, 3491-3496. Article: (IV) Ritzén, A.; Frejd, T. Cyclisation of meta-phenylene-bis-alanine derivatives J. Chem. Soc., Perkin Trans. 1 1998, 3419-3424. Article: (V) Ritzén, A.; Frejd, T. Synthesis of a chiral dendrimer based on polyfunctional amino acids J. Chem. Soc., Chem. Commun. 1999, 207-208. Article: (VI) Ritzén, A; Frejd, T. Chiral, Polyionic Dendrimers with Complementary Charges. Synthesis and Chiroptical Properties In manuscript. The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- 8a6606c5-758f-4a9e-a6ec-b6ecde73d8b4 (old id 40186)
- date added to LUP
- 2016-04-04 11:16:37
- date last changed
- 2018-11-21 21:03:47
@phdthesis{8a6606c5-758f-4a9e-a6ec-b6ecde73d8b4,
abstract = {{A number of protected aromatic bis- and tris(amino acids) have been synthesised by catalytic asymmetric hydrogenation of the corresponding didehydroamino acid derivatives. The didehydroamino acid derivatives were prepared either by a Heck coupling of a 2-amidoacrylate with an aryl dihalide, or by Horner-Wadsworth-Emmons olefination of aromatic aldehydes with phosphonylglycine reagents. Excellent stereochemical purity could be achieved in most cases.<br/><br>
<br/><br>
The bis- and tris(amino acids) were then used as building blocks in a model study, the purpose of which was to assess the feasibility of constructing synthetic receptors from tris(amino acids). Several macrocyclic peptide-like compounds were prepared.<br/><br>
<br/><br>
Chiral dendrimers were also synthesised from the bis- and tris(amino acids). These dendrimers could be deprotected to yield water-soluble, polycationic or polyanionic macromolecules with a common structure. A chiroptical study of the protected dendrimers was undertaken, and it indicated that the solution shape is rather flat and sterically uncongested.}},
author = {{Ritzén, Andreas}},
keywords = {{Organisk kemi; Organic chemistry; HWE reaction; asymmetric hydrogenation; Heck reaction; Amino acids; chiral dendrimers}},
language = {{eng}},
publisher = {{Department of Organic Chemistry, Lund University}},
school = {{Lund University}},
title = {{Synthesis of aromatic bis- and tris(amino acids) and chiral dendrimers}},
year = {{1999}},
}