A practical synthesis of gramicidin S and sugar amino acid containing analogues

被引：41

作者：

Grotenbreg, GM

Kronemeijer, M

Timmer, MSM

El Oualid, F

van Well, RM

Verdoes, M

Spalburg, E

van Hooft, PAV

de Neeling, AJ

Noort, D

van Boom, JH

van der Marel, GA

Overkleeft, HS

Overhand, M

机构：

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

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

[3] TNO, Prins Maurits Lab, NL-2280 AA Rijswijk, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 23期

关键词：

D O I：

10.1021/jo0487449

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical gram-scale and high-yielding synthesis of the antimicrobial peptide gramicidin S is presented. An Fmoc-based solid-phase peptide synthesis protocol is employed for the generation of the linear decapeptide precursor, which is cyclized in solution to afford the target compound. The versatility of our method is demonstrated by the construction of eight gramicidin S analogues (15ah) having nonproteinogenic sugar amino acid residues (4-7) incorporated in the turn regions.

引用

页码：7851 / 7859

页数：9

共 44 条

[1] Aguilera B, 2001, EUR J ORG CHEM, V2001, P1541, DOI 10.1002/1099-0690(200104)2001:8<1541::AID-EJOC1541>3.0.CO
[2] 2-7
[3] 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
[4] Metal catalyzed diazo transfer for the synthesis of azides from amines
Alper, PB
Hung, SC
Wong, CH
[J]. TETRAHEDRON LETTERS, 1996, 37 (34) : 6029 - 6032
[5] IBTM-containing gramicidin S analogues: Evidence for IBTM as a suitable type II' beta-turn mimetic
Andreu, D
Ruiz, S
Carreno, C
Alsina, J
Albericio, F
Jimenez, MA
delaFiguera, N
Herranz, R
GarciaLopez, MT
GonzalezMuniz, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) : 10579 - 10586
[6] Spatially close porphyrin pair linked by the cyclic peptide Gramicidin S
Arai, T
Maruo, N
Sumida, Y
Korosue, C
Nishino, N
[J]. CHEMICAL COMMUNICATIONS, 1999, (16) : 1503 - 1504
[7] Activation method to prepare a highly reactive acylsulfonamide ''safety-catch'' linker for solid-phase synthesis
Backes, BJ
Virgilio, AA
Ellman, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) : 3055 - 3056
[8] Synthesis of gramicidin S and its analogues via an on-resin macrolactamization assisted by a predisposed conformation of the linear precursors
Bu, XZ
Wu, XM
Ng, NLJ
Mak, CK
Qin, CG
Guo, ZH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) : 2681 - 2685
[9] CASTRO B, 1975, TETRAHEDRON LETT, P1219
[10] Sugar amino acids and their uses in designing bioactive molecules
Chakraborty, TK
Ghosh, S
Jayaprakash, S
[J]. CURRENT MEDICINAL CHEMISTRY, 2002, 9 (04) : 421 - 435

← 1 2 3 4 5 →