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Synthesis of Amino Acids with Unnatural Nucleobases or Chromophores Suitable for Use in Model Electron‐Transfer Studies
Author(s) -
Wagner Thomas,
Davis William B.,
Lorenz Katrin B.,
MichelBeyerle Maria E.,
Diederichsen Ulf
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300242
Subject(s) - chemistry , nucleobase , chromophore , amino acid , covalent bond , electron transfer , side chain , diimide , combinatorial chemistry , stereochemistry , organic chemistry , dna , molecule , polymer , biochemistry , perylene
We describe the syntheses of Boc‐protected amino acids bearing the chromophores pyromellitic diimide, naphthalene diimide, and pyrene in their side chains, as well as nucleo amino acids with the artificial purines 7‐carbaguanine, 7‐carbaadenine, isoadenine, and 7‐carbaisoadenine covalently linked to the alanyl side chain. These amino acids incorporating chromophores are suitable building blocks for incorporation into alanyl‐PNA for future investigations of the mechanism of nucleobase‐mediated electron transfer. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)