title: Tetrahydropyranyl, a nonaromatic acid-labile Cys protecting group for Fmoc peptide chemistry.
abstract: Tetrahydropyranyl (Thp), which exploits the concept of being an S,O-acetal nonaromatic protecting group for cysteine, has been shown to be superior to Trt, Dpm, Acm, and StBu in solid-phase peptide synthesis using the Fmoc/tBu strategy. Thus, Cys racemization and C-terminal 3-(1-piperidinyl)alanine formation were minimized when the Cys was protected with Thp. This nonaromatic protecting group also improved the solubility of Cys-containing protected peptides.
authors.affiliation: †Institute for Research in Biomedicine, 08028 Barcelona, Spain.|‡Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain.
authors.forename: Iván
authors.initials: I
authors.lastname: Ramos-Tomillero
authors.affiliation: †Institute for Research in Biomedicine, 08028 Barcelona, Spain.|§School of Chemistry, Yachay Tech, Yachay City of Knowledge, 100199 Urcuqui, Ecuador.
authors.forename: Hortensia
authors.initials: H
authors.lastname: Rodríguez
authors.affiliation: †Institute for Research in Biomedicine, 08028 Barcelona, Spain.|‡Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain.|§School of Chemistry, Yachay Tech, Yachay City of Knowledge, 100199 Urcuqui, Ecuador.|∥CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, 08028 Barcelona, Spain.|⊥School of Chemistry, University of KwaZulu Natal, 4000 Durban, South Africa.
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques
chemical_list: C000602109:3-(1-piperidinyl)alanine; D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; D011714:Pyrans; D003545:Cysteine; D000409:Alanine