Fluorous (trimethylsilyl)ethanol: a new reagent for carboxylic acid tagging and protection in peptide synthesis.
Starting with a fluorous analogue of 2-(trimethylsilyl)ethanol, we have designed an easy method for preparing a new fluorous tag ((F)TMSE) for the protection of carboxylic acids. Because mild conditions are employed in the tag cleavage (TBAF in the presence of 4 A molecular sieves, which prevent racemization), this tag can be advantageously used in the synthesis of peptides and modified peptides, as we have demonstrated with several examples, including the fluorous synthesis of short alpha- and beta-peptides as well as of modified fluorinated retropeptides.
Fustero
Santos
S
Departamento de Química Organica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
García Sancho
Amador
A
Chiva
Gema
G
Sanz-Cervera
Juan F
JF
del Pozo
Carlos
C
Aceña
José Luis
JL
D002264:Carboxylic Acids / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D002264:Carboxylic Acids; D010455:Peptides; D014297:Trimethylsilyl Compounds