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Enantioselective synthesis of new conformationally constrained sugar-like gamma-, delta-, epsilion-amino acids, delta-peptides and nucleoside amino acids

URN to cite this document: urn:nbn:de:bvb:355-opus-5968

Haque, Mohammad Mahbubul (2006) Enantioselective synthesis of new conformationally constrained sugar-like gamma-, delta-, epsilion-amino acids, delta-peptides and nucleoside amino acids. PhD, Universität Regensburg

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Abstract (English)

The new conformationally constrained sugar-like gamma-, delta-, and epsilon-amino acids were synthesized in enantiomerically pure in an efficient manner from trans-2,3-disubstituted gamma-butyrolactone These novel amino acids can serve as useful templates to induce interesting secondary structures in peptides. Furthermore, the novel delta-peptide was synthesized from conformationally constrained Boc-delta-amino acid via an iterative peptide coupling strategy. Finally, a new strategy was developed leading to the nucleoside amino acid starting from the amine (5-Allyl-4-[(4-methoxy-benzylamino)-methyl]-dihydro-furan. The introduction of pyrimidine base onto the lactone followed by oxidation of the allyl double bond as key steps. This novel nucleoside amino acid can serve as useful building block towards PNA analogue synthesis.

Translation of the abstract (German)

Neue, konformationell eingeschränkte zuckerartige gamma-, delta-, und epsilon-Aminosäuren wurden enantiomerenrein in effizienter Weise aus trans-2,3-disubstituierten gamma-Butyrolactonen synthetisiert. Diese neuartigen Aminosäuren dienen als nützliche Template zur Einführung interessanter Sekundärstrukturen in Peptiden. Desweiteren wurden neue delta-Peptide aus konformationell eingeschränkten Boc-delta-Aminosäuren über eine iterative Strategie der Peptid kupplung dargestellt. Außerdem wurde auch eine neue Strategie zur Darstellung von Nucleosid-aminosäuren, ausgehend von (5-Allyl-4-[(4-methoxy-benzylamino)-methyl]-dihydro-furan, entwickelt. Die Einführung der Pyrimidin base in die Lactonstruktur gefolgt von einer Oxidation der allylischen Doppelbindung, stellten die Schlüsselschritte dieser Synthese dar. Diese neuen Nucleosid-aminosäuren stellen nützliche Bausteine zur Synthese von PNA-Analoga dar.

Item Type:Thesis of the University of Regensburg (PhD)
Referee:Oliver (Prof. Dr.) Reiser
Date of exam:27 October 2005
Institutions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Keywords:Zuckeranaloga , Aminosäuren , Nukleinsäuren , Assymetrische Synthese , Zuckeranaloge Aminosäuren , Aminosäuren , delta-Peptide , Nukleosid Aminosäuren , Sugar amino acids , amino acids , delta peptide , Nucleoside amino acid
Subjects:500 Science > 540 Chemistry & allied sciences
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Yes
Owner:Universitätsbibliothek Regensburg
Deposited On:27 Oct 2009 08:41
Last Modified:05 Nov 2012 09:09
Item ID:10405
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