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Nucleo‐ β ‐Amino Acids: Synthesis and Oligomerization to β ‐Homoalanyl‐PNA
Author(s) -
Brückner Arndt M.,
Schmitt Harald W.,
Diederichsen Ulf
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200211)85:11<3855::aid-hlca3855>3.0.co;2-a
Subject(s) - chemistry , nucleobase , amino acid , stereochemistry , mitsunobu reaction , nucleophilic substitution , nucleic acid , derivative (finance) , nucleophile , combinatorial chemistry , organic chemistry , biochemistry , catalysis , dna , financial economics , economics
The synthesis of thyminyl‐, uracilyl‐, cytosinyl‐, and guaninyl‐ β 3 ‐amino acids and the oligomerization of the cytosinyl‐ and guaninyl‐ β 3 ‐amino acids to β ‐homoalanyl‐PNA are presented. The pyrimidinyl nucleobases were connected to the γ ‐position of β ‐homoalanine by Mitsunobu reaction with a β ‐homoserine derivative or by nucleophilic substitution of methanesulfonates. For the preparation of the guaninyl‐ β 3 ‐amino acid, a β ‐lactam route was established that might be of interest also for the synthesis of other β 3 ‐amino acid derivatives. The cytosinyl and guaninyl building blocks were oligomerized to hexamers. They form quite stable self‐pairing complexes in H 2 O as indicated by temperature dependent UV and CD spectroscopy.