𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of Amino-Acid-Derived Nucleo(side/tide) Analogs for Peptide-Derived Enantiospecific Nucleic Acid Analogs

✍ Scribed by Vibhakar J. Shah; Irwin D. Kuntz; Jr.; George L. Kenyon

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
186 KB
Volume
24
Category
Article
ISSN
0045-2068

No coin nor oath required. For personal study only.

✦ Synopsis

A convergent and cost-effective strategy to synthesize enantiospecific nucleoside/ nucleotide analogs from readily available Ͱ-amino acids has been described. Both (L)-and (D)-methionine were transformed in four steps to the corresponding key intermediates (L)-and (D)-2-(tertbutyloxycarbonylamino)-4-bromomethyl butyrate. Nucleophilic displacement of the bromide by nucleic acid bases (e.g., adenine, thymine, guanine, cytosine) provided the enantiomerically pure monomers required for the solid-phase synthesis of novel peptide-derived enantiospecific nucleic acid analogs.

📜 SIMILAR VOLUMES

Solid-Phase Synthesis of Peptide-Derived
Solid-Phase Synthesis of Peptide-Derived Enantiospecific Nucleic Acid Analogs
✍ Vibhakar J. Shah; Robert Cerpa; Irwin D. Kuntz; Jr.; George L. Kenyon 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 207 KB

The first solid-phase synthesis of novel peptide-derived enantiospecific nucleic acid analogs (PDNAs), employing all three stereoisomers of 4-(N 9 -adeninyl)-2-amino(t-boc)-butyric acid as ADNA (amino acid-derived nucleoside analogs) monomers has been described. The preliminary melting temperature (

Synthesis of Alaninyl and N-(2-Aminoethy
Synthesis of Alaninyl and N-(2-Aminoethyl)glycinyl Amino Acid Derivatives Containing the Green Fluorescent Protein Chromophore in Their Side Chains for Incorporation into Peptides and Peptide Nucleic Acids
✍ Thorsten Stafforst; Ulf Diederichsen 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 English ⚖ 294 KB 👁 1 views

## Abstract Artificial amino acids carrying either the chromophore of the Green Fluorescent Protein (GFP) or a modification as their side chains have been synthesized: Boc‐protected alaninyl derivatives and Fmoc‐protected __N__‐(2‐aminoethyl)glycine‐functionalized amino acids were obtained and coul

ChemInform Abstract: Two Novel Amino Aci
ChemInform Abstract: Two Novel Amino Acid Derivatives Containing Side-Chain Thioamides for the Synthesis of Photoactivatable Peptides.
✍ P. SINGH; C. R. HURRELL; J. B. C. FINDLAY; C. W. G. FISHWICK 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 2 views

Two Novel Amino Acid Derivatives Containing Side-Chain Thioamides for the Synthesis of Photoactivatable Peptides. -An efficient method to obtain novel amino acid derivatives (V), which can be introduced into peptides by solid-phase standard procedures, is described. -

Enantioselective Synthesis of β-Amino Ac
Enantioselective Synthesis of β-Amino Acids, Part 13 : Diastereoselective Alkylation of Dianions Derived from Chiral Analogs of β-Aminopropanoic Acid Containing the α-Phenylethyl Group
✍ Víctor Manuel Gutiérrez-García; Gloria Reyes-Rangel; Omar Muñoz-Muñiz; Eusebio J 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 German ⚖ 129 KB

## Abstract Inexpensive acryloyl chloride was converted in 91% overall yield to two derivatives of __β__‐alanine, (__R__,__R__,__R__)‐**6** and (__R__,__R__,__S__)‐**6**, containing two chiral auxiliaries. __C__‐Alkylation of (__R__,__R__,__R__)‐ and (__R__,__R__,__S__)‐**6** __via__ a dianion deri