Benzotriazole-Mediated Synthesis of Aza-peptides: En Route to an Aza-Leuenkephalin Analogue

被引：20

作者：

Abo-Dya, Nader E. ^{[1
,2
]}

Biswas, Suvendu ^{[1
]}

Basak, Akash ^{[1
]}

Avan, Ilker ^{[1
,3
]}

Alamry, Khalid A. ^{[4
]}

Katritzky, Alan R. ^{[1
,4
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Zagazig Univ, Dept Organ Pharmaceut Chem, Fac Pharm, Zagazig 44519, Egypt

[3] Anadolu Univ, Dept Chem, TR-26470 Eskisehir, Turkey

[4] King Abdulaziz Univ, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 08期

关键词：

BETA-TURN FORMATION; AMINO-ACIDS; CYSTEINE PROTEASES; LEUKOCYTE ELASTASE; AZAPEPTIDES; DIPEPTIDES; INHIBITORS; POTENT; INACTIVATION; SCAN;

D O I：

10.1021/jo302251e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel N-(N-Pg-azadipeptidoyl)benzotriazoles 20a-e couple efficiently with alpha-amino acids 21a-e, dipeptides 22a-c, aminoxyacetic acid 23a, depsidipeptide 23b, and alpha-hydroxy-beta-phenylpropionic acid 27 yielding, respectively, azatripeptides 24a-g, azatetrapeptides 25a,b, a hybrid azatripeptide with an oxyamide bond 26a, a hybrid azatetrapeptide with an ester bond 26b, and a hybrid azatripeptide with an ester bond 28. A new protocol for the synthesis of N-Pg-azatripeptides 33a,b and 35a,b, each containing a natural amino acid at the N-terminus, avoids the low coupling rates of the aza-amino acid residue and enables the solution-phase synthesis of an azaphenylalanine analogue of Leu-enkephalin 40.

引用

页码：3541 / 3552

页数：12

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