Synthesis of Nucleo Aminooxy Acid Derivatives

被引:10
作者
Noel, Olivier [1 ]
Xie, Juan [1 ]
机构
[1] ENS Cachan, PPSM, Inst Alembert, CNRS,UMR 8531, F-94235 Cachan, France
来源
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 01期
关键词
nucleo aminooxy acids; nucleopeptides; N-oxy nucleopeptides; cytosine; thymine; amides; triazoles; L-serine; eliminations; PEPTIDE; DESIGN; INHIBITION; MONOMERS; HELICES; PNAS;
D O I
10.1055/s-0032-1317689
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nucleobase-functionalized peptides have attracted increasing interest because of their well-ordered secondary structures and stability toward enzymatic degradations. We have designed and synthesized nucleo aminooxy acids as novel building blocks for nucleopeptides. Four nucleo aminooxy acid derivatives with cytosine or thymine in the side chain linked by an amide or a triazole moiety have been synthesized from L-serine.
引用
收藏
页码:134 / 140
页数:7
相关论文
共 26 条
[1]   Three-dimensional organization of helices:: Design principles for nucleobase-functionalized β-peptides [J].
Chakraborty, P ;
Diederichsen, U .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (11) :3207-3216
[2]   Controlling the outcome of overacylation of N-protected aminooxyacetic acid during the synthesis of an aminooxy-peptide for chemical ligation [J].
Decostaire, Isidore P. ;
Lelievre, Dominique ;
Zhang, Haihui ;
Delmas, Agnes F. .
TETRAHEDRON LETTERS, 2006, 47 (39) :7057-7060
[3]   Pairing properties of alanyl peptide nucleic acids containing an amino acid backbone with alternating configuration [J].
Diederichsen, U .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :445-448
[4]  
Diederichsen U, 1998, ANGEW CHEM INT EDIT, V37, P302, DOI 10.1002/(SICI)1521-3773(19980216)37:3<302::AID-ANIE302>3.0.CO
[5]  
2-4
[6]   SYNTHESIS OF PEPTIDE NUCLEIC-ACID MONOMERS CONTAINING THE 4 NATURAL NUCLEOBASES - THYMINE, CYTOSINE, ADENINE, AND GUANINE AND THEIR OLIGOMERIZATION [J].
DUEHOLM, KL ;
EGHOLM, M ;
BEHRENS, C ;
CHRISTENSEN, L ;
HANSEN, HF ;
VULPIUS, T ;
PETERSEN, KH ;
BERG, RH ;
NIELSEN, PE ;
BUCHARDT, O .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5767-5773
[7]   α-helical peptide nucleic acids (αPNAs):: A new paradigm for DNA-binding molecules [J].
Garner, P ;
Dey, S ;
Huang, YM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2405-2406
[8]   Design and synthesis of intrinsically cell-penetrating nucleopeptides [J].
Geotti-Bianchini, Piero ;
Beyrath, Julien ;
Chaloin, Olivier ;
Formaggio, Fernando ;
Bianco, Alberto .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (20) :3661-3663
[9]   Replacement of Ala by Aib improves structuration and biological stability in thymine-based α-nucleopeptides [J].
Geotti-Bianchini, Piero ;
Moretto, Alessandro ;
Peggion, Cristina ;
Beyrath, Julien ;
Bianco, Alberto ;
Formaggio, Fernando .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (06) :1315-1321
[10]   Conformationally controlled, thymine-based α-nucleopeptides [J].
Geotti-Bianchini, Piero ;
Crisma, Marco ;
Peggion, Cristina ;
Bianco, Alberto ;
Formaggio, Fernando .
CHEMICAL COMMUNICATIONS, 2009, (22) :3178-3180