Protection process of the tert-butyl group as a non-polar moiety of D-serine: unexpected rearrangement.
The use of amino acid derivatives as building blocks in peptide synthesis is increasingly being recognized as a potential route for the development of pharmaceutical agents. Side chain protection of polyfunctional amino acids such as Ser, Thr, Tyr is viewed as being particularly important. Although these derivatives are commercially listed, they are expensive and not widely available. We describe here a practical large-scale synthesis of t-butyl introduced D-serine, one of the building blocks of zoladex, a peptide drug.
Choi
B E
BE
College of Pharmacy, Kyung Hee University, Seoul , Korea.
Jeong
J H
JH
D000081:Acetamides / Q000737:chemistry; D007202:Indicators and Reagents; D010455:Peptides / Q000138:chemical synthesis; D012694:Serine / Q000031:analogs & derivatives* / Q000737:chemistry*
D000081:Acetamides; D007202:Indicators and Reagents; D010455:Peptides; D012694:Serine