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The p ‐Nitrocinnamyloxycarbonyl (Noc) Moiety—an Acid‐stable Amino‐protecting Group Removable under Neutral Conditions for Peptide and Glycopeptide Synthesis
Author(s) -
Kunz Horst,
März Joachim
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198813751
Subject(s) - moiety , protecting group , amino acid , chemistry , glycopeptide , cleavage (geology) , catalysis , peptide , stereochemistry , group (periodic table) , combinatorial chemistry , organic chemistry , biochemistry , materials science , fracture (geology) , composite material , alkyl , antibiotics
The bond between the new protecting group 1 and the amino groups of amino acids is very acid stable . However, it can be easily and quantitatively cleaved under almost neutral conditions by Pd 0 catalysis. Further advantages of the protecting group 1 are its strong UV absorption and its stability in the Rh I ‐catalyzed cleavage of “normal” allyl protecting groups; in addition, the amino acids containing these protecting groups are almost always crystalline.