d-Peptide Analogues of Pyranosyl-RNA, Part 1 , Nucleo-d-peptides Derived from Conformationally Constrained Nucleo-d-amino Acids: Preparation of Monomers

d-Peptide Analogues of Pyranosyl-RNA, Part 1 , Nucleo-d-peptides Derived from Conformationally Constrained Nucleo-d-amino Acids: Preparation of Monomers

Cyclic nucleo-amino acids that constitute monomers of a conformationally constrained nucleo-peptide base-pairing system have been prepared. Their synthesis starts with an enantioselectively catalyzed chirogenic Diels-Alder reaction, proceeds via a regioselective -iodolactamization process, and ends...

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Bibliographic Details
Published in:Helvetica chimica acta Vol. 83; no. 6; pp. 1049 - 1078
Main Authors: Karig, Gunter, Fuchs, Andreas, Busing, Arne, Brandstetter, Tilmann, Scherer, Stefan, Bats, Jan W, Eschenmoser, Albert, Quinkert, Gerhard
Format: Journal Article
Language:English
Published: 07-06-2000
Online Access:Get full text
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Summary:Cyclic nucleo-amino acids that constitute monomers of a conformationally constrained nucleo-peptide base-pairing system have been prepared. Their synthesis starts with an enantioselectively catalyzed chirogenic Diels-Alder reaction, proceeds via a regioselective -iodolactamization process, and ends with a regio- as well as diastereoselective introduction of nucleobases through SN2-type opening of a transiently formed N-acylaziridine ring. Extensive use of X-ray crystal-structure analysis has been made to support structure assignments.
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ISSN:0018-019X
DOI:10.1002/1522-2675(20000607)83:6<1049::AID-HLCA1049>3.0.CO;2-1