C-terminal incorporation of α-trifluoromethyl-substituted amino acids into peptides via in-situ deprotection of N-Teoc derivatives

被引：0

作者：

Hollweck, W ^{[1
]}

Sewald, N ^{[1
]}

Michel, T ^{[1
]}

Burger, K ^{[1
]}

机构：

[1] Univ Leipzig, Dept Organ Chem, D-04103 Leipzig, Germany

来源：

LIEBIGS ANNALEN-RECUEIL | 1997年 / 12期

关键词：

alpha-amino acids; Teoc-protected alpha-trifluoromethyl-substituted; Fmoc amino acid fluorides; peptidomimetics;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new method for peptide coupling, involving alpha-trifluoromethyl substituted amino acids as nucleophiles, proceeds via fluoride catalyzed in situ deprotection and coupling of N-Teoc protected amino acid esters. A mixed anhydride is thought to be the reaction intermediate.

引用

页码：2549 / 2551

页数：3

共 14 条

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BURGER, K
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HOLLWECK, W
KOKSCH, B
LIEBIGS ANNALEN DER CHEMIE, 1994, (04): : 407 - 413
[2] PEPTIDE MODIFICATION BY INCORPORATION OF ALPHA-TRIFLUOROMETHYL ALPHA-AMINO-ACIDS VIA TRIFLUOROMETHYL-SUBSTITUTED ACYLIMINES
HOSS, E
RUDOLPH, M
SEYMOUR, L
SCHIERLINGER, C
BURGER, K
JOURNAL OF FLUORINE CHEMISTRY, 1993, 61 (1-2) : 163 - 170
[3] Incorporation of α-trifluoromethyl substituted α-amino acids into C- and N-terminal position of peptides and peptide mimetics using multicomponent reactions
Burger, K
Mütze, K
Hollweck, W
Koksch, B
TETRAHEDRON, 1998, 54 (22) : 5915 - 5928
[4] The Prebiotic C-Terminal Elongation of Peptides Can Be Initiated by N-Carbamoyl Amino Acids
Abou Mrad, Ninette
Ajram, Ghinwa
Rossi, Jean-Christophe
Boiteau, Laurent
Duvernay, Fabrice
Pascal, Robert
Danger, Gregoire
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (31) : 7418 - 7421
[5] A METHOD FOR IDENTIFYING C-TERMINAL AMINO ACIDS AS THEIR DNS-DERIVATIVES OBTAINED AFTER HYDRAZINOLYSIS OF PEPTIDES
NEDKOV, P
GENOV, N
BIOCHIMICA ET BIOPHYSICA ACTA, 1966, 127 (02) : 544 - &
[6] TETRAZOLE ANALOGUES OF AMINO ACIDS AND PEPTIDES .5. SYNTHESES OF PEPTIDE DERIVATIVES CONTAINING TETRAZOLE ANALOGUES OF AMINO ACIDS IN C-TERMINAL POSITION
GRZONKA, Z
REKOWSKA, E
LIBEREK, B
TETRAHEDRON, 1971, 27 (11) : 2317 - &
[7] SIMULTANEOUS DETERMINATION OF N- AND C-TERMINAL AMINO ACIDS IN POLYPEPTIDES - SELECTIVE TRITIATION OF DNP-PEPTIDES
MATSUO, H
FUJIMOTO, Y
TATSUNO, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1967, 15 (05) : 716 - +
[8] SEQUENTIAL POLYPEPTIDES - SYNTHESIS OF N-PROTECTED, C-ACTIVATED PEPTIDES FROM C-TERMINAL RESIDUES OF AMINO ACIDS
KAPOOR, A
GERENCSER, LW
JOURNAL OF PHARMACEUTICAL SCIENCES, 1969, 58 (08) : 976 - +
[9] PHASE-TRANSFER REAGENTS AS C-TERMINAL PROTECTING GROUPS - FACILE INCORPORATION OF FREE AMINO-ACIDS OR PEPTIDES INTO PEPTIDE SEQUENCES
CHEN, ST
WANG, KT
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (15) : 1045 - 1047
[10] Computational study of complexes between mercury (II) and tetra-peptides with N- and C-terminal cysteine amino acids
Nichols, Diamond
Watts, Joshua
Merle, John K.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245

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