𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Simple and efficient solid-phase synthesis of unprotected peptide aldehyde for peptide segment ligation

✍ Scribed by Dominique Lelièvre; Hadjila Chabane; Agnès Delmas

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
217 KB
Volume
39
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

We describe an efficient solid-phase synthesis of C-terminal peptide aldehyde. Making use of the stability of the PAM linker towards both acid and base conditions, a pentapeptide was synthesized starting from a PAM resin according to Fmoe/tBu chemistry. The side-chains were deprotected by TFA. The peptide was cleaved by aminolysis with aminoacetaldehyde-dimethylacetal leading to a C-terminal masked aldehyde. The unprotected peptide aldehyde was then coupled to amino-oxy derivatives by chemoseleetive ligation in aqueous solution.

📜 SIMILAR VOLUMES

Peptide thioester preparation by Fmoc so
Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation
✍ Andrew B. Clippingdale; Colin J. Barrow; John D. Wade 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 135 KB 👁 2 views

Established methodology for the preparation of peptide thioesters requires the use of t-butoxycarbonyl chemistry owing to the lability of thioester linkers to the nucleophilic reagents used in Fmoc solid phase peptide synthesis. Both the greater ease of use and the broad applicability of the method

Solid phase synthesis of peptide C-termi
Solid phase synthesis of peptide C-terminal semicarbazones and aldehydes
✍ Jennifer A. Patterson; Robert Ramage 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 179 KB

A new linker based on the dibenzosuberyl system was developed in order to synthesis¢ peptide Cterminal semicarbazones which can b¢ readily converted into peptide (7-terminal aldehydes. The method uses Fmoc-methodoiogy and proceeds with no loss of stereochemical integrity.

Multimeric Cyclic RGD Peptides as Potent
Multimeric Cyclic RGD Peptides as Potential Tools for Tumor Targeting: Solid-Phase Peptide Synthesis and Chemoselective Oxime Ligation
✍ Georgette Thumshirn; Ulrich Hersel; Simon L. Goodman; Horst Kessler 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 English ⚖ 206 KB 👁 2 views

## Abstract The __α__v__β__3 integrin receptor plays an important role in human metastasis and tumor‐induced angiogenesis. Targeting this receptor may provide information about the receptor status of the tumor and enable specific therapeutic planning. Solid‐phase peptide synthesis of multimeric __c

Solid phase synthesis of a ΨCH2NH pseudo
Solid phase synthesis of a ΨCH2NH pseudopeptide by ligation of a peptidyl aldehyde with a resin-bound amino peptide
✍ Christel Gros; Nathalie Galéotti; Robert Pascal; Patrick Jouin 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 571 KB

Solid phase synthesis of W[CH2NH] pseudopeptide 3 was accomplished by reductive amination of peptidyl aldehyde 1 with resin bound amino peptide 2. No epimerization took place during the aldehyde preparation or the reductive amination step. This convergent strategy should facilitate the synthesis of