𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Saponification of esters of chiral α-amino acids anchored through their amine function on solid support

✍ Scribed by Sonia Cantel; Stéphane Desgranges; Jean Martinez; Jean-Alain Fehrentz

Book ID
105360372
Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
72 KB
Volume
10
Category
Article
ISSN
1075-2617

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Anchoring an α‐amino acid residue by its amine function onto a solid support is an alternative to develop chemistry on its carboxylic function. This strategy can involve the use of amino‐acid esters as precursors of the carboxylic function. A complete study on the Wang‐resin was performed to determine the non‐racemizing saponification conditions of anchored α‐amino esters. The use of LiOH, NaOH, NaOSi(Me)~3~, various solvents and temperatures were tested for this reaction. After saponification and cleavage from the support, samples were examined through their Marfey's derivatives by reversed phase HPLC to evaluate the percentage of racemization. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.

📜 SIMILAR VOLUMES

Synthesis of chiral α-amino aldehydes li
Synthesis of chiral α-amino aldehydes linked by their amine function to solid support
✍ Sonia Cantel; Annie Heitz; Jean Martinez; Jean-Alain Fehrentz 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 English ⚖ 73 KB

## Abstract The anchoring of an α‐amino‐acid derivative by its amine function on to a solid support allows some chemical reactions starting from the carboxylic acid function. This paper describes the preparation of α‐amino aldehydes linked to the support by their amine function. This was performed

An Efficient Synthesis of Achiral and Ch
An Efficient Synthesis of Achiral and Chiral Cyclic Dehydro-α-Amino Acid Derivatives Through Nucleophilic Addition of Amines to β,γ-Unsaturated α-Keto Esters.
✍ Francisco Palacios; Javier Vicario; Domitila Aparicio 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 25 KB

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

An Efficient Synthesis of Achiral and Ch
An Efficient Synthesis of Achiral and Chiral Cyclic Dehydro-α-Amino Acid Derivatives Through Nucleophilic Addition of Amines to β,γ-Unsaturatedα-Keto Esters
✍ Francisco Palacios; Javier Vicario; Domitila Aparicio 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 English ⚖ 156 KB

## Abstract A very simple and efficient synthesis of 3‐amino‐1,5‐dihydro‐2__H__‐pyrrol‐2‐ones is reported. These cyclic dehydro‐amino acid derivatives with a stereogenic center at the 5‐position were obtained by the addition of two equivalents of amine to β,γ‐unsaturated keto esters. These cyclic e

Liquid chromatographic enantiomer resolu
Liquid chromatographic enantiomer resolution of N-fluorenylmethoxycarbonyl α-amino acids and their ester derivatives on polysaccharide-derived chiral stationary phases
✍ Yin Hua Li; Wonjae Lee 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 English ⚖ 101 KB

## Abstract The liquid chromatographic enantiomer separation of __N__‐fluorenylmethoxycarbonyl (FMOC) protected α‐amino acids and their ethyl ester derivatives was performed on polysaccharide‐derived chiral stationary phases, Chiralcel OD, Chiralpak AD, and Chiralpak AS. In general, Chiralcel OD an