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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 09期

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

页码：1349 / 1352

页数：4

共 41 条

[1] Design and asymmetric synthesis of beta-strand peptidomimetics [J].

Boumendjel, A ;

Roberts, JC ;

Hu, E ;

Pallai, PV ;

Rebek, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4434-4438

[2] Development of 5-(aminomethyl)pyrrole-2-carboxylic acid as a constrained surrogate of Gly-ΔAla and its application in peptidomimetic studies [J].

Chakraborty, TK ;

Mohan, BK ;

Kumar, SK ;

Kunwar, AC .

TETRAHEDRON LETTERS, 2002, 43 (14) :2589-2592

[3] CHEMISTRY OF PYRROLIC COMPOUNDS .4. BETA-HYDROXY- AND BETA-METHOXY-PYRROLES [J].

CHONG, R ;

CLEZY, PS .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1967, 20 (05) :935-&

[4] Control of hairpin formation via proline configuration in parallel β-sheet model systems [J].

Fisk, JD ;

Powell, DR ;

Gellman, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (23) :5443-5447

[5] Mimetics of the Peptide β-Strand [J].

Glenn, Matthew P. ;

Fairlie, David P. .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2002, 2 (05) :433-445

[6] Stereochemical requirements for beta-hairpin formation: Model studies with four-residue peptides and depsipeptides [J].

Haque, TS ;

Little, JC ;

Gellman, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6975-6985

[7] Insights on beta-hairpin stability in aqueous solution from peptides with enforced type I' and type II' beta-turns [J].

Haque, TS ;

Gellman, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2303-2304

[8] Promotion of sheet formation in α-peptide strands by a β-peptide reverse turn [J].

Huck, BR ;

Fisk, JD ;

Gellman, SH .

ORGANIC LETTERS, 2000, 2 (17) :2607-2610

[9] Folding of an artificial β-sheet in competitive solvents [J].

Junquera, E ;

Nowick, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2527-2531

[10] SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF EPINDOLIDIONE-DERIVED PEPTIDE MODELS FOR BETA-SHEET FORMATION [J].

KEMP, DS ;

BOWEN, BR ;

MUENDEL, CC .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4650-4657

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