THE N-IM-(2,4-DIMETHYLPENT-3-YLOXYCARBONYL) (DOC) GROUP, A NEW NUCLEOPHILE-RESISTANT, HF-CLEAVABLE PROTECTING GROUP FOR HISTIDINE IN PEPTIDE-SYNTHESIS

Authors
KARLSTROM A UNDEN A
Citation
A. Karlstrom et A. Unden, THE N-IM-(2,4-DIMETHYLPENT-3-YLOXYCARBONYL) (DOC) GROUP, A NEW NUCLEOPHILE-RESISTANT, HF-CLEAVABLE PROTECTING GROUP FOR HISTIDINE IN PEPTIDE-SYNTHESIS, Chemical communications, (8), 1996, pp. 959-960
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Chemical communications → ACNP
ISSN journal
13597345
Issue
8
Year of publication
1996
Pages
959 - 960
Database
ISI
SICI code
1359-7345(1996):8<959:TN(GAN>2.0.ZU;2-W
Abstract
The 2,4-dimethylpent-3-yloxycarbonyl group as protection for the imida zole ring of histidine combines several properties that makes it ideal for solid phase peptide synthesis with Boc chemistry; it is readily c leaved by liquid HF, stable to trifluoroacetic acid, soluble in apolar organic solvents and highly resistant to nucleophiles, thereby avoidi ng the danger of N-im to N-alpha transfer and premature cleavage by ot her nucleophiles during solid phase synthesis.