Synthesis of enantiomerically enriched 4,5-disubstituted N-aminoimidazol-2-one (Nai) peptide turn mimics

被引：3

作者：

Poupart, Julien ^{[1
]}

Hamdane, Yousra ^{[1
]}

Lubell, William D. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Succursale Ctr Ville, Montreal, PQ H3C 3J7, Canada

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2020年 / 98卷 / 06期

基金：

加拿大自然科学与工程研究理事会;

关键词：

N-aminoimidazolone; peptide mimicry; Vilsmeier formylation; 5-endo-dig cyclization; beta-turn; AMINO-ACIDS; CONFORMATION; DERIVATIVES; DESIGN; LACTAM;

D O I：

10.1139/cjc-2019-0479

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Aminoimidazolone (Nai) peptide mimics were synthesized with minimal epimerization by base-promoted 5-endo-dig cyclization of aza-propargylglycine dipeptide acids and hydrazides followed by olefin migration. 5-Position functionalization using Mannich amino methylation and Vilsmeier-Haack formylation has given access to a set of restrained side chain analogs of Asp, Dab, and Hse residues for mimicry of turn form and function.

引用

页码：278 / 284

页数：7

共 35 条

[1] A REINVESTIGATION OF MIXED CARBONIC ANHYDRIDE METHOD OF PEPTIDE SYNTHESIS [J].

ANDERSON, GW ;

ZIMMERMAN, JE ;

CALLAHAN, FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (19) :5012-+

[2] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].

BAL, BS ;

CHILDERS, WE ;

PINNICK, HW .

TETRAHEDRON, 1981, 37 (11) :2091-2096

[3] Synthesis of Imidazolidin-2-ones and Imidazol-2-ones via Base-Catalyzed Intramolecular Hydroamidation of Propargylic Ureas under Ambient Conditions [J].

Casnati, Alessandra ;

Perrone, Antonio ;

Mazzeo, Paolo P. ;

Bacchi, Alessia ;

Mancuso, Raffaella ;

Gabriele, Bartolo ;

Maggi, Raimondo ;

Maestri, Giovanni ;

Motti, Elena ;

Stirling, Andras ;

Della Ca', Nicola .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (06) :3477-3490

[4] Azapeptide Synthesis Methods for Expanding Side-Chain Diversity for Biomedical Applications [J].

Chingle, Ramesh ;

Proulx, Caroline ;

Lubell, William D. .

ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (07) :1541-1556

[5] Molecular recognition with designed peptides and proteins [J].

Cooper, WJ ;

Waters, ML .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2005, 9 (06) :627-631

[6] Peptide therapeutics: current status and future directions [J].

Fosgerau, Keld ;

Hoffmann, Torsten .

DRUG DISCOVERY TODAY, 2015, 20 (01) :122-128

[7] BIOACTIVE CONFORMATION OF LUTEINIZING-HORMONE-RELEASING HORMONE - EVIDENCE FROM A CONFORMATIONALLY CONSTRAINED ANALOG [J].

FREIDINGER, RM ;

VEBER, DF ;

PERLOW, DS ;

BROOKS, JR ;

SAPERSTEIN, R .

SCIENCE, 1980, 210 (4470) :656-658

[8] PROTECTED LACTAM-BRIDGED DIPEPTIDES FOR USE AS CONFORMATIONAL CONSTRAINTS IN PEPTIDES [J].

FREIDINGER, RM ;

PERLOW, DS ;

VEBER, DF .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) :104-109

[9] Synthesis of hydrazine and azapeptide derivatives by alkylation of carbazates and semicarbazones [J].

Garcia-Ramos, Yesica ;

Proulx, Caroline ;

Lubell, William D. .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2012, 90 (11) :985-993

[10] Diversity-Oriented Syntheses of β-Substituted α-Amino γ-Lactam Peptide Mimics with Constrained Backbone and Side Chain Residues [J].

Geranurimi, Azade ;

Lubell, William D. .

ORGANIC LETTERS, 2018, 20 (19) :6126-6129

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