A study of the cis-trans isomerization preference of N-alkylated peptides containing phosphorus in the side chain and backbone

被引：12

作者：

de la Torre, Alexander F. ^{[1
]}

Ali, Akbar ^{[2
]}

Concepcion, Odette ^{[1
]}

Montero-Alejo, Ana L. ^{[3
,4
]}

Muniz, Francisco M. ^{[1
]}

Jimenez, Claudio A. ^{[1
]}

Belmar, Julio ^{[1
]}

Luis Velazquez-Libera, Jose ^{[5
]}

Hernandez-Rodriguez, Erix W. ^{[6
]}

Caballero, Julio ^{[5
]}

机构：

[1] Univ Concepcion, Fac Ciencias Quim, Dept Quim Organ, Concepcion, Chile

[2] Univ Sargodha, Dept Chem, Sargodha 40100, Pakistan

[3] Univ Tecnol Metropolitana, FCNMM, Dept Fis, Jose Pedro Alessandri 1242, Santiago 7800002, Chile

[4] Nucl Milenio MULTIMAT, Santiago, Chile

[5] Univ Talca, CBSM, 1 Poniente 1141, Talca, Chile

[6] Univ Catolica Maule, Fac Med, Escuela Quim & Farm, Talca 3460000, Chile

来源：

NEW JOURNAL OF CHEMISTRY | 2019年 / 43卷 / 32期

关键词：

ANTIBACTERIAL AGENTS; PEPTOIDS; PHOSPHONOPEPTIDES; DESIGN; NITROGEN; AMIDES; ACID; KEY;

D O I：

10.1039/c9nj02234a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The current work provides a study on the cis-trans isomerization behaviour of N-alkylated peptides decorated with phosphonate ester groups. A Ugi four-component reaction was chosen for the synthesis of N-alkylated peptides, where almost only the cis isomer was detected when the phosphonate ester group was incorporated as an amine component in the side chain. However, the phosphonate ester group inserted in the backbone, as an isocyanide component, leads preferably to the trans isomer of this kind of peptides. The diverse behaviour of cis-trans isomerization has been explained via spectroscopic nuclear magnetic resonance analysis and computational calculations.

引用

页码：12804 / 12813

页数：10

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