Synthesis and application of Fmoc-His(3-Bum)-OH.
This paper presents a reevaluation of the synthesis and properties of Fmoc-His(3-Bum)-OH regarding its application in SPPS with minimal racemization of histidine residues during coupling and esterification reactions. By-product formation during the deprotection of the test peptides could be significantly reduced by scavenging the concomitantly formed HCHO, e.g. with methoxyamine.
Mergler
M
M
BACHEM AG, Bubendorf, Switzerland.
Dick
F
F
Sax
B
B
Schwindling
J
J
Vorherr
T H
TH
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D006639:Histidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010452:Peptide Biosynthesis; D021241:Spectrometry, Mass, Electrospray Ionization
D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; C450041:fluorenylmethoxycarbonyl-histidinyl(3-t-butyloxymethyl)hydroxide; D006639:Histidine