A side-reaction in the SPPS of Trp-containing peptides.
Syntheses of several Trp-containing peptides on a Wang solid support afforded significant amounts of a side-product. 1H-NMR and MS data showed that an unexpected alkylation by the linker has occurred on the indole nucleus. This was observed whatever the scavenger used, and whatever the position of the Trp residue in the sequence, unless it was in the C-terminal position.
Giraud
M
M
Laboratoire des Aminoacides, Peptides et Protéines, UMR-CNRS 5810, Universités Montpellier I et II UM II, CC19, France.
Cavelier
F
F
Martinez
J
J
D000595:Amino Acid Sequence; D001671:Biochemistry / Q000379:methods; D002853:Chromatography, Liquid / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D014364:Tryptophan / Q000737:chemistry*
D010455:Peptides; D014364:Tryptophan