𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Solid-phase synthesis of Nα-benzyl-Nα-cinnamyl lysine and glutamic acid derivatives

✍ Scribed by Peter J Connolly; Kimberly N Beers; Steven K Wetter; William V Murray

Book ID
104210512
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
224 KB
Volume
41
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Several variations of a solid-phase strategy for the synthesis of N a -benzyl-N a -cinnamyl lysine and glutamic acid derivatives are presented. Starting from the corresponding N a -Fmoc amino acids on Wang resin, reductive alkylation using nitrocinnamaldehyde or a substituted benzaldehyde was followed by nucleophilic displacement of a substituted benzyl halide or nitrocinnamyl bromide to provide resin-bound intermediates. Diversity was added by reduction of the nitro group and derivatization of the resulting aminocinnamyl moiety with a variety of acylating or sulfonylating reagents. Using an orthogonal protecting group strategy, N e -Dde-protected lysine derivatives were further functionalized at the side-chain amino group prior to cleavage from resin. This method allows for the preparation of analog libraries having up to four points of diversity.

📜 SIMILAR VOLUMES

Synthesis of Nα-Boc-Nε-tetrabenzyl-DTPA-
Synthesis of Nα-Boc-Nε-tetrabenzyl-DTPA-L-lysine and Nα-Fmoc-Nε-tetra-t-butyl-DTPA-L-lysine, building blocks for solid phase synthesis of DTPA-containing peptides
✍ Dr John S. Davies; Loai Al-Jamri 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 127 KB

## Abstract Two building blocks, Boc‐Lys(Bn~4~‐DTPA)‐OH and Fmoc‐Lys($\hbox{Bu}^{\rm t}\_{4}$‐DTPA)‐OH have been synthesized via the acylation of the ε‐amino group of __N__^α^‐protected lysine, using suitably protected tetra‐esters of diethylene triamine pentaacetic acid (DTPA), a ligand with wide