Amino Acid Building Blocks for Efficient Fmoc Solid-Phase Synthesis of Peptides Adenylylated at Serine or Threonine

被引：7

作者：

Albers, Michael F. ^{[1
]}

van Vliet, Bart ^{[1
]}

Hedberg, Christian ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 22期

关键词：

AMPYLATION; SYNTHETASE;

D O I：

10.1021/ol2024696

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first straightforward building block based (non-interassembly) synthesis of peptides containing adenylylated serine and threonine residues Is described. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The described Thr-AMP SPPS-building block has been employed in the synthesis of the Thr-adenylylated sequence of human GTPase CDC42 (Ac-SEYVP-T(AMP)-VFDNYGC-NH2). Further, we demonstrate proof-of-concept for the synthesis of an Ser-adenylylated peptide (Ac-GSGA-S(AMP)-AGSGC-NH2) from the corresponding adenylylated serine building block.

引用

页码：6014 / 6017

页数：4

共 17 条

[1] Chemical synthesis of Ser/Thr AMPylated peptides
Al-Eryani, Rwaida A.
Li, Yan
Ball, Haydn L.
[J]. TETRAHEDRON LETTERS, 2010, 51 (13) : 1730 - 1731
[2] 1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE
CARPINO, LA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) : 4397 - 4398
[3] NEW ALLYL GROUP ACCEPTORS FOR PALLADIUM-CATALYZED REMOVAL OF ALLYLIC PROTECTIONS AND TRANSACYLATION OF ALLYL CARBAMATES
DESSOLIN, M
GUILLEREZ, MG
THIERIET, N
GUIBE, F
LOFFET, A
[J]. TETRAHEDRON LETTERS, 1995, 36 (32) : 5741 - 5744
[4] O-BENZOTRIAZOLYL-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE AS COUPLING REAGENT FOR THE SYNTHESIS OF PEPTIDES OF BIOLOGICAL INTEREST
DOURTOGLOU, V
GROSS, B
LAMBROPOULOU, V
ZIOUDROU, C
[J]. SYNTHESIS-STUTTGART, 1984, (07): : 572 - 574
[5] Solid-phase synthesis of peptide and glycopeptide thioesters through side-chain-anchoring strategies
Ficht, Simon
Payne, Richard J.
Guy, Richard T.
Wong, Chi-Huey
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (12) : 3620 - 3629
[6] Characterization of a rabbit polyclonal antibody against threonine-AMPylation
Hao, Yi-Heng
Chuang, Trinette
Ball, Haydn L.
Luong, Phi
Li, Yan
Flores-Saaib, Ruben D.
Orth, Kim
[J]. JOURNAL OF BIOTECHNOLOGY, 2011, 151 (03) : 251 - 254
[7] A critical electrostatic interaction mediates inhibitor recognition by human asparagine synthetase
Ikeuchi, Hideyuki
Meyer, Megan E.
Ding, Yun
Hiratake, Jun
Richards, Nigel G. J.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (18) : 6641 - 6650
[8] Adenylylation: renaissance of a forgotten post-translational modification
Itzen, Aymelt
Blankenfeldt, Wulf
Goody, Roger S.
[J]. TRENDS IN BIOCHEMICAL SCIENCES, 2011, 36 (04) : 219 - 226
[9] GTPases involved in vesicular trafficking: Structures and mechanisms
Itzen, Aymelt
Goody, Roger S.
[J]. SEMINARS IN CELL & DEVELOPMENTAL BIOLOGY, 2011, 22 (01) : 48 - 56
[10] Fido, a Novel AMPylation Domain Common to Fic, Doc, and AvrB
Kinch, Lisa N.
Yarbrough, Melanie L.
Orth, Kim
Grishin, Nick V.
[J]. PLOS ONE, 2009, 4 (06):

← 1 2 →