Nanometer-Sized Amino Acids for the Synthesis of Nanometer-Scale Water-Soluble Molecular Rods of Precise Length

@article{citeulike:2762826, abstract = {Abstract: This paper introduces the unnatural amino acid Abc2K as a nanometer-length building block for the creation of water-soluble molecular rods of exceptional size. Abc2K is a water-soluble variant of the unnatural amino acid 4'-amino-[1,1'-biphenyl]-4-carboxylic acid (Abc) with lysinelike propyloxyammonium side chains at the 2- and 5-positions. The protected building block Fmoc-Abc2K(Boc)-OH (1) can be used in standard Fmoc-based solid-phase peptide synthesis to create water-soluble rodlike peptides in nanometer unit lengths up to at least ten nanometers. Oligomers up to and including the decamer were easily prepared on a Rink amide resin. These peptides are easy to purify and characterize by standard reverse-phase HPLC, 1H NMR, and ESI-MS techniques. The Abc2K amino acid can be combined with various standard amino acids to provide well behaved hybrid and biologically relevant peptides. Building block 1 is efficiently prepared on a multigram scale from commercially available starting materials by way of the Suzuki cross-coupling reaction. Molecular modeling studies of Abc2K oligomers show only minor effects from torsional and bending motions and support a model in which the oligomers are relatively straight and rigid. Fluorescence resonance energy transfer (FRET) studies are consistent with a model in which the Abc2K oligomers behave as rigid rods with a length of 1.0 nm per monomer unit.}, address = {Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025}, author = {Gothard, C. M. and Rao, N. A. and Nowick, J. S. }, citeulike-article-id = {2762826}, doi = {10.1021/ja072648i}, journal = {J. Am. Chem. Soc.}, keywords = {origami, origami-alternatives}, month = {June}, number = {23}, pages = {7272--7273}, posted-at = {2008-05-06 21:21:14}, priority = {2}, title = {Nanometer-Sized Amino Acids for the Synthesis of Nanometer-Scale Water-Soluble Molecular Rods of Precise Length}, url = {http://dx.doi.org/10.1021/ja072648i}, volume = {129}, year = {2007} }

TY - JOUR ID - citeulike:2762826 TI - Nanometer-Sized Amino Acids for the Synthesis of Nanometer-Scale Water-Soluble Molecular Rods of Precise Length JF - J. Am. Chem. Soc. VL - 129 IS - 23 SP - 7272 EP - 7273 AD - Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025 N2 - Abstract: This paper introduces the unnatural amino acid Abc2K as a nanometer-length building block for the creation of water-soluble molecular rods of exceptional size. Abc2K is a water-soluble variant of the unnatural amino acid 4'-amino-[1,1'-biphenyl]-4-carboxylic acid (Abc) with lysinelike propyloxyammonium side chains at the 2- and 5-positions. The protected building block Fmoc-Abc2K(Boc)-OH (1) can be used in standard Fmoc-based solid-phase peptide synthesis to create water-soluble rodlike peptides in nanometer unit lengths up to at least ten nanometers. Oligomers up to and including the decamer were easily prepared on a Rink amide resin. These peptides are easy to purify and characterize by standard reverse-phase HPLC, 1H NMR, and ESI-MS techniques. The Abc2K amino acid can be combined with various standard amino acids to provide well behaved hybrid and biologically relevant peptides. Building block 1 is efficiently prepared on a multigram scale from commercially available starting materials by way of the Suzuki cross-coupling reaction. Molecular modeling studies of Abc2K oligomers show only minor effects from torsional and bending motions and support a model in which the oligomers are relatively straight and rigid. Fluorescence resonance energy transfer (FRET) studies are consistent with a model in which the Abc2K oligomers behave as rigid rods with a length of 1.0 nm per monomer unit. KW - origami KW - origami-alternatives AU - Gothard, CM AU - Rao, NA AU - Nowick, JS PY - 2007/06/13/ UR - http://dx.doi.org/10.1021/ja072648i ER -