Design and Synthesis of Gramicidin S Analogs with High Antibiotic Activity

被引：1

作者：

Sato, Kazuki ^{[1
]}

Yamaguchi, Yoko ^{[1
]}

Nagai, Ukon ^{[2
]}

机构：

[1] Fukuoka Womens Univ, Dept Environm Sci, Higashi Ku, Fukuoka 8138529, Japan

[2] Mitsubishi Kagaku Inst Life Sci, Machida, Tokyo 1948511, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2013年 / 86卷 / 01期

关键词：

BETA-TURN PREFERENCES; 4TH AMINO-ACIDS; CD SPECTRA; TETRAPEPTIDE SEQUENCES; CONFORMATIONAL PROPERTIES; PEPTIDES; PART; DERIVATIVES; 1ST;

D O I：

10.1246/bcsj.20120166

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Based on the beta-turn preference of tetrapeptide sequences as analyzed by CD spectra of their chromophoric derivatives, 10 analogs of gramicidin S (GS) were designed and synthesized with general formula cyclo(-D-Leu(1,1')-D-Lys(2,2')-D-Leu(3,3')-L-Pro(4,4')-X-5,X-5'-)(2), where X is L-Asn, L-Ala, L-Leu, L-Phe, L-cyclohexylalanine, Gly, D-Ala, D-Leu, D-Phe, or D-cyclohexylalanine. Several analogs with high hydrophobicity showed antibiotic activity as strong as GS. CD spectra of the analogs with D-amino acid or Gly at the X position and their dinitrophenyl derivatives suggested that they have beta-sheet conformation that is antipodal to that of GS.

引用

页码：112 / 120

页数：9

共 24 条

[1]

CORNISHBOWDEN A, 1984, EUR J BIOCHEM, V138, P9, DOI 10.1111/j.1432-1033.1984.tb07877.x

[2] STUDIES ON THE BETA-TURN OF PEPTIDES .6. NUCLEAR MAGNETIC-RESONANCE STUDY ON THE CONFORMATIONS OF N-(2,4-DINITROPHENYL)TETRAPEPTIDE PARA-NITROANILIDES RELATED TO THE BETA-TURN PART OF GRAMICIDIN-S [J].

HIGASHIJIMA, T ;

SATO, K ;

NAGAI, U .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (11) :3323-3328

[3]

IZUMIYA N, 1979, SYNTHETIC ASPECTS BI, pCH4

[4] Proline residue-modified polycationic analogs of gramicidin S with high antibacterial activity against both Gram-positive and Gram-negative bacteria and low hemolytic activity [J].

Kawai, M ;

Yamamura, H ;

Tanaka, R ;

Umemoto, H ;

Ohmizo, C ;

Higuchi, S ;

Katsu, T .

JOURNAL OF PEPTIDE RESEARCH, 2005, 65 (01) :98-104

[5] STUDIES ON THE BETA-TURN OF PEPTIDES .5. TURN PREFERENCE OF PEPTIDE SEQUENCES ANALYZED BY CONFORMATIONAL ENERGY CALCULATION ON DIPEPTIDE MODELS AND BY CD SPECTRA OF CHROMOPHORIC DERIVATIVES [J].

KAWAI, M ;

SATO, K ;

SUGAWARA, R ;

NAGAI, U .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (10) :3005-3008

[6]

KAWAI M, 1984, INT J PEPT PROT RES, V24, P607

[7] COMPARISON OF CONFORMATION AND ANTI-MICROBIAL ACTIVITY OF SYNTHETIC ANALOGS OF GRAMICIDIN-S - STEREOCHEMICAL CONSIDERATION OF ROLE OF D-PHENYLALANINE IN ANTIBIOTIC [J].

KAWAI, M ;

NAGAI, U .

BIOPOLYMERS, 1978, 17 (06) :1549-1565

[8] STUDIES OF PEPTIDE ANTIBIOTICS .8. SYNTHESIS OF GLY4,4'-GRAMICIDIN S [J].

NAGATA, R ;

WAKI, M ;

KONDO, M ;

AOYAGI, H ;

KATO, T ;

MAKISUMI, S ;

IZUMIYA, N .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (04) :963-+

[9] STUDIES ON THE BETA-TURN OF PEPTIDES .8. BETA-TURN PREFERENCES OF N-ACETYLTETRAPEPTIDE METHYLAMIDES RELATED TO THE BETA-TURN PART OF GRAMICIDIN-S [J].

SATO, K ;

HIGASHIJIMA, T ;

SUGAWARA, R ;

NAGAI, U .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (12) :3699-3702

[10]

SATO K, 1984, INT J PEPT PROT RES, V24, P600

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