Synthesis and peptide binding properties of methoxypyrrole amino acids (MOPAS)

被引:24
作者
Bonauer, C [1 ]
Zabel, M [1 ]
König, B [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem & Zent Analyt, D-93040 Regensburg, Germany
关键词
D O I
10.1021/ol049855x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methoxypyrrole amino acids (MOPAS) have been prepared and were introduced into small peptides with hairpin structures. The intra- and intermolecular binding properties of this heterocyclic amino acid mimicking a dipeptido beta-strand was investigated by NMR titration and X-ray crystal structure analysis. The data reveal a hydrogen bonding pattern that is complementary to a peptide beta-sheet.
引用
收藏
页码:1349 / 1352
页数:4
相关论文
共 41 条
[21]   Triurea derivatives of diethylenetriamine as potential templates for the formation of artificial beta-sheets [J].
Nowick, JS ;
Mahrus, S ;
Smith, EM ;
Ziller, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) :1066-1072
[22]   Sequence-selective molecular recognition between β sheets [J].
Nowick, JS ;
Chung, DM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1765-1768
[23]   Three-stranded mixed artificial β-sheets [J].
Nowick, JS ;
Smith, EM ;
Ziller, JW ;
Shaka, AJ .
TETRAHEDRON, 2002, 58 (04) :727-739
[24]   An unnatural amino acid that induces β-sheet folding and interaction in peptides [J].
Nowick, JS ;
Lam, KS ;
Khasanova, TV ;
Kemnitzer, WE ;
Maitra, S ;
Mee, HT ;
Liu, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :4972-4973
[25]   MOLECULAR SCAFFOLDS .3. AN ARTIFICIAL PARALLEL BETA-SHEET [J].
NOWICK, JS ;
SMITH, EM ;
NORONHA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7386-7387
[26]   Artificial beta-sheets [J].
Nowick, JS ;
Smith, EM ;
Pairish, M .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (06) :401-&
[27]   An unnatural amino acid that mimics a tripeptide β-strand and forms β-sheetlike hydrogen-bonded dimers (vol 122, pg 7654, 2000) [J].
Nowick, JS ;
Chung, DM ;
Maitra, K ;
Maitra, S ;
Stigers, KD ;
Sun, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (07) :1545-1545
[28]   An extended beta-strand mimic for a larger artificial beta-sheet [J].
Nowick, JS ;
Pairish, M ;
Lee, IQ ;
Holmes, DL ;
Ziller, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (23) :5413-5424
[29]   Chemical models of protein β-sheets [J].
Nowick, JS .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (04) :287-296
[30]   A triply templated artificial β-sheet [J].
Nowick, JS ;
Cary, JM ;
Tsai, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5176-5180