p-Chlorotetrafluorophenyl esters of N-protected amino acids.
p-Chlorotetrafluorophenyl (Tfc) esters of protected amino acids and peptides are more reactive than are the well known pentafluorophenyl (Pfp) esters. Two reagents, p-chlorotetrafluorophenyltrifluoroacetate (Tfc-OTfa) and di-(p-chlorotetrafluorophenyl)carbonate (di-Tfc-carbonate), can be used for their syntheses, thereby avoiding use of the allergic dicyclohexylcarbodiimide. This is especially important for bulk preparations. Many Fmoc- and Boc-amino acid-OTfc esters have been synthesized and characterized. The hexadecameric tandem repeat H-(AlaAlaLysPro)4-OH was synthesized using di-Tfc-carbonate for the preparation of Tfc-esters.
Medvedkin
V N
VN
Institute of Protein Research, Russian Academy of Science, Pushchino, Moscow Region.
Klimenko
L N
LN
Mitin
Y V
YV
Kretsinger
R H
RH
Shabanowitz
J
J
Zabolotskikh
V F
VF
Podgornova
N N
NN
D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry; D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry; D005464:Fluorobenzenes / Q000737:chemistry; D005563:Formic Acid Esters / Q000737:chemistry; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis*; D012091:Repetitive Sequences, Nucleic Acid
D000596:Amino Acids; C092684:Boc-alanine 4-chlorotetrafluorophenyl ester; D004952:Esters; D005449:Fluorenes; D005464:Fluorobenzenes; D005563:Formic Acid Esters; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D009842:Oligopeptides; D010455:Peptides; C000345:t-butyloxycarbonyl group; D000409:Alanine