Ethylcarbamoyl protection for cysteine in the preparation of peptide-conjugate immunogens.
During the solid-phase synthesis of over 100 peptides, we have observed that the ethylcarbamoyl group is useful for the side chain protection of cysteine in peptides containing a single cysteine residue. The ethylcarbamoyl group is stable to the conditions of acidolytic cleavage, purification and long term storage. Brief treatment of peptides containing an S-ethylcarbamoyl-cysteine residue with aqueous sodium hydroxide gives the deprotected cysteine peptide that can be coupled to carrier molecules such as proteins to give immunogen conjugates.
Blake
J
J
Bristol-Myers Squibb, Seattle, WA.
Woodworth
B A
BA
Litzi-Davis
L
L
Cosand
W L
WL
D000595:Amino Acid Sequence; D003545:Cysteine / Q000031:analogs & derivatives / Q000737:chemistry*; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D014520:Urethane / Q000737:chemistry*; D014614:Vaccines, Synthetic / Q000737:chemistry*
D010455:Peptides; D014614:Vaccines, Synthetic; D014520:Urethane; D003545:Cysteine