Amino Acid Building Blocks for Fmoc Solid-Phase Synthesis of Peptides Phosphocholinated at Serine, Threonine, and Tyrosine

被引：7

作者：

Albers, Michael F. ^{[1
]}

Hedberg, Christian ^{[1
]}

机构：

[1] Max Planck Inst Mol Physiol, Dept Biol Chem, D-44227 Dortmund, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期

关键词：

RAB GTPASE FUNCTION; LEGIONELLA; PROTEINS;

D O I：

10.1021/jo302587g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phosphocholination of eukaryotic host cell proteins has recently been identified as a novel post-translational modification important for bacterial pathogenesis. Here, we describe the first straightforward synthetic strategy for peptides containing phosphocholinated serine, threonine, or tyrosine residues using preformed functional amino acid building blocks, fully compatible with standard Fmoc solid-phase peptide synthesis.

引用

页码：2715 / 2719

页数：5

共 50 条

[21] FMOC SOLID-PHASE SYNTHESIS OF SERINE PHOSPHOPEPTIDES VIA SELECTIVE PROTECTION OF SERINE AND ON RESIN PHOSPHORYLATION
SHAPIRO, G
SWOBODA, R
STAUSS, U
TETRAHEDRON LETTERS, 1994, 35 (06) : 869 - 872
[22] Synthesis ofC-Glycosyl Amino Acid Building Blocks Suitable for the Solid-Phase Synthesis of Multivalent Glycopeptide Mimics
Reintjens, Niels R. M.
Koemans, Tony S.
Zilverschoon, Nick
Castelli, Riccardo
Cordfunke, Robert A.
Drijfhout, Jan Wouter
Meeuwenoord, Nico J.
Overkleeft, Herman S.
Filippov, Dmitri, V
van der Marel, Gijsbert A.
Codee, Jeroen D. C.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (32) : 5126 - 5139
[23] ALTERNATIVE STRATEGIES FOR THE FMOC SOLID-PHASE SYNTHESIS OF O-4-PHOSPHO-L-TYROSINE-CONTAINING PEPTIDES
KITAS, EA
KNORR, R
TRZECIAK, A
BANNWARTH, W
HELVETICA CHIMICA ACTA, 1991, 74 (06) : 1314 - 1328
[24] Synthesis of a Fluorinated Sialophorin Hexasaccharide-Threonine Conjugate for Fmoc Solid-Phase Glycopeptide Synthesis
Daum, Markus
Broszeit, Frederik
Hoffmann-Roeder, Anja
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (22) : 3709 - 3720
[25] Solid-phase synthesis of new S-glycoamino acid building blocks
Jobron, L
Hummel, G
ORGANIC LETTERS, 2000, 2 (15) : 2265 - 2267
[26] FMOC-AMINO ACID CHLORIDES-KOBT IN SOLID-PHASE PEPTIDE-SYNTHESIS
SIVANANDAIAH, KM
BABU, VVS
GANGADHAR, BP
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1994, 33 (07): : 620 - 623
[27] A NOVEL FMOC-BASED ANCHORAGE FOR THE SYNTHESIS OF PROTECTED PEPTIDES ON SOLID-PHASE
LIU, YZ
DING, SH
CHU, JY
FELIX, AM
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1990, 35 (02): : 95 - 98
[28] Fmoc solid-phase synthesis of c-terminal diketopiperazine thioester peptides
Nakajima, Yuya
Nakatsu, Koki
Hayashi, Gosuke
Murakami, Hiroshi
JOURNAL OF PEPTIDE SCIENCE, 2024, 30
[29] Nα-Fmoc-O,O-(dimethylphospho)-L-tyrosine fluoride: A convenient building block for the solid-phase synthesis of phosphotyrosyl peptides
Fretz H.
Letters in Peptide Science, 1997, 4 (3): : 171 - 176
[30] Nα-Fmoc-O,O-(dimethylphospho)-L-tyrosine fluoride: A convenient building block for the solid-phase synthesis of phosphotyrosyl peptides
Heinz Fretz
Letters in Peptide Science, 1997, 4 (3): : 171 - 176

← 1 2 3 4 5 →