Synthesis and biological evaluation of novel turn-modified gramicidin S analogues

被引：30

作者：

Grotenbreg, GM

Spalburg, E

de Neeling, AJ

van der Marel, GA

Overkleeft, HS

van Boom, JH

Overhand, M

机构：

[1] Gorlaeus Labs, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands

[2] Natl Inst Publ Hlth & Environm, Res Lab Infect Dis, NL-3720 BA Bilthoven, Netherlands

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2003年 / 11卷 / 13期

关键词：

D O I：

10.1016/S0968-0896(03)00219-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of novel gramicidin S analogues having additional functionalities in the turn region by employing a biomimetic approach is described. The preservation of beta-sheet character in all analogues was established by NMR and the biological activity was evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：2835 / 2841

页数：7

共 23 条

[1] THE SYNTHESIS OF A HEAVY-ATOM DERIVATIVE OF GRAMICIDIN-S (GS), [D-PHE(4-BR)4,4']-GS, BY A NOVEL METHOD
AIMOTO, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (06) : 2220 - 2222
[2] Castro B., 1975, Tetrahedron Lett, V16, P1219, DOI [10.1016/S0040-4039(00)72100-9, DOI 10.1016/S0040-4039(00)72100-9]
[3] FLORSHEIMER A, 1991, PEPTIDES 1990, P131
[4] GANGAMANI BP, 1991, TETRAHEDRON, V34, P2787
[5] Gramicidin Sand its use in the treatment of infected wounds
Gause, GF
Brazhnikova, MG
[J]. NATURE, 1944, 154 : 703 - 703
[6] Unusual β-sheet periodicity in small cyclic peptides
Gibbs, AC
Kondejewski, LH
Gronwald, W
Nip, AM
Hodges, RS
Sykes, BD
Wishart, DS
[J]. NATURE STRUCTURAL BIOLOGY, 1998, 5 (04) : 284 - 288
[7] Probing the structural determinants of type II′ β-turn formation in peptides and proteins
Gibbs, AC
Bjorndahl, TC
Hodges, RS
Wishart, DS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1203 - 1213
[8] CRYSTAL-STRUCTURE OF A HYDRATED GRAMICIDIN S UREA COMPLEX
HULL, SE
KARLSSON, R
MAIN, P
WOOLFSON, MM
DODSON, EJ
[J]. NATURE, 1978, 275 (5677) : 206 - 207
[9] Diastereoisomeric analogues of gramicidin S: structure, biological activity and interaction with lipid bilayers
Jelokhani-Niaraki, M
Kondejewski, LH
Farmer, SW
Hancock, REW
Kay, CM
Hodges, RS
[J]. BIOCHEMICAL JOURNAL, 2000, 349 : 747 - 755
[10] Total synthesis and antifungal evaluation of cyclic aminohexapeptides
Klein, LL
Li, LP
Chen, HJ
Curty, CB
DeGoey, DA
Grampovnik, DJ
Leone, CL
Thomas, SA
Yeung, CM
Funk, KW
Kishore, V
Lundell, EO
Wodka, D
Meulbroek, JA
Alder, JD
Nilius, AM
Lartey, PA
Plattner, JJ
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (07) : 1677 - 1696

← 1 2 3 →