𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of β-pyrazinyl-L-alanine (Paa) and of peptide derivatives

✍ Scribed by Claudia Petermann; Jean-Luc Fauchère

Book ID
102252880
Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
370 KB
Volume
66
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The title compound was prepared via a malonic ester synthesis starting with α‐chloromethylpyrazine [2], and ending, after an asymmetric enzymatic hydrolysis of the racemic N‐acetyl‐β‐2‐pyrazinylalanine to the L‐form of the new amino acid. The optical purity was ascertained by ^1^H‐NMR analysis at 360 MHz of the diastereoisomeric dipeptides L‐pyrazinylalanine‐L‐leucine and D‐pyrazinylalanine‐L‐leucine. Hydrophobic, steric and electronic parameters for its side chain were also estimated, which can be useful for the quantitative study of structure‐activity relationships of biologically active peptide derivatives. The new amino acid could be introduced in the place of phenylalanine in the enkephalin‐like pentapeptide [D‐alanyl^2^, leucine^5^]enkephalin, thus showing good stability towards the classical methods of peptide synthesis.

📜 SIMILAR VOLUMES

Synthesis of β-Tetrazolyl DL-Alanine Der
Synthesis of β-Tetrazolyl DL-Alanine Derivatives
✍ Alami, A.; El Hallaoui, A.; Elachqar, A.; Hajji, S. El; Roumestant, M. L.; Viall 📂 Article 📅 1998 🏛 Taylor and Francis Group 🌐 English ⚖ 316 KB
Efficient synthesis of β-halogeno protec
Efficient synthesis of β-halogeno protected l-alanines and their β-phosphonium derivatives
✍ Franck Meyer; Abdelhamid Laaziri; Anna Maria Papini; Jacques Uziel; Sylvain Jugé 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 265 KB

Ring opening of oxazolines, prepared from L-serinates, with trimethylsilyl halides (TMSX) led to b-halogeno-N-benzoyl-a-amino esters in good to excellent yields. Quaternization of triphenylphosphine by the b-bromo or -iodo amino esters gave the corresponding b-phosphonium salts in overall yields of