Flow-chemistry enabled efficient synthesis of β-peptides: backbone topology vs. helix formation

被引：13

作者：

Nekkaa, Imane ^{[1
]}

Bogdan, Dora ^{[2
]}

Gati, Tamas ^{[2
,3
]}

Beni, Szabolcs ^{[4
]}

Juhasz, Tunde ^{[5
]}

Palko, Marta ^{[1
]}

Paragi, Gabor ^{[6
,7
]}

Toth, Gabor K. ^{[6
,7
]}

Fulop, Ferenc ^{[1
]}

Mandity, Istvan M. ^{[1
,2
,8
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, Eotvos U 7, H-6720 Szeged, Hungary

[2] Semmelweis Univ, Dept Organ Chem, Fac Pharm, Hogyes Endre U 7, H-1092 Budapest, Hungary

[3] SRIMC, Zahony Utca 7, H-1031 Budapest, Hungary

[4] Semmelweis Univ, Dept Pharmacognosy, Fac Pharm, Ulloi Ut 26, H-1085 Budapest, Hungary

[5] Hungarian Acad Sci, Inst Mat & Environm Chem, Res Ctr Nat Sci, Magyar Tudosok Krt 2, H-1117 Budapest, Hungary

[6] Univ Szeged, Dept Med Chem, Dom T 8, H-6720 Szeged, Hungary

[7] MTA SZTE Biomimet Syst Res Grp, Dom T 8, H-6720 Szeged, Hungary

[8] Hungarian Acad Sci, MTA TTK Lendulet Artificial Transporter Res Grp, Inst Mat & Environm Chem, Res Ctr Nat Sci, Magyar Tudosok Krt 2, H-1117 Budapest, Hungary

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 21期

关键词：

AMINO-ACID; SECONDARY STRUCTURE; FOLDAMER HELICES; DESIGN; SELECTIVITY; STABILITY; OLIGOMERS; MIMETICS;

D O I：

10.1039/c8cc10147g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiodiscriminative helix formation was observed for beta-peptide H14 helices. This observation is caused by the synperiplanar orientation of H-O atoms which is more unfavorable than those for H-H interaction. The 1,2 H-O interaction leads to the destruction of the helical structure. The introduction of a double C-C bond in the backbone rules out helix formation.

引用

页码：3061 / 3064

页数：4