Gramicidin S: Relationship of Cyclic Structure to Antibiotic Activity

Nature ◽  
1954 ◽  
Vol 174 (4435) ◽  
pp. 840-841 ◽  
Author(s):  
BERNARD F. ERLANGER ◽  
LOUISE GOODE
Keyword(s):  
Antibiotic Activity ◽  
Cyclic Structure ◽  
Gramicidin S ◽  
Relationship Of

scholarly journals First Draft Genome Sequence of Thermophilic Laceyella tengchongensis BKK01, Isolated from Municipal Solid Waste in Thailand

2020 ◽  
Vol 9 (37) ◽  
Author(s):  
Sirirat Wachiralurpan ◽  
Pattarawan Ruangsuj ◽  
Wariya Yamprayoonswat ◽  
Pattarawut Sopha ◽  
Watthanachai Jumpathong ◽  
...  
Keyword(s):  
Municipal Solid Waste ◽  
Solid Waste ◽  
Genome Sequence ◽  
Draft Genome ◽  
Thermophilic Bacterium ◽  
Antibiotic Activity ◽  
Draft Genome Sequence ◽  
Content Type ◽  
Gramicidin S ◽  
Bacteria And Fungi

ABSTRACT Laceyella tengchongensis BKK01 is a thermophilic bacterium isolated from municipal solid waste. The genome of L. tengchongensis BKK01 includes a gene putatively encoding gramicidin S synthase. Gramicidin S has antibiotic activity against some bacteria and fungi. The newly sequenced 3.44-Mb draft genome of L. tengchongensis BKK01 will shed some light on the biosynthesis of gramicidin S.

scholarly journals Isoepoxydon, a new metabolite of the patulin pathway in Penicillium urticae

1979 ◽  
Vol 182 (2) ◽  
pp. 445-453 ◽  
Author(s):  
Junichi Sekiguchi ◽  
G. Maurice Gaucher
Keyword(s):  
Parent Strain ◽  
Biosynthetic Pathway ◽  
Secondary Alcohol ◽  
Antibiotic Activity ◽  
Epoxide Ring ◽  
Boat Conformation ◽  
Washed Cell ◽  
Washed Cell Suspension ◽  
Relationship Of ◽  
Better Than

A patulin-negative mutant (J1) of Penicillium urticae (N.R.R.L. 2159A) was known to accumulate about 100mg per litre quantities of the 5,6-epoxygentisyl quinone, (−)-phyllostine and another metabolite (UIII). Both were derived from acetate and hence were polyketides. Purified UIII (m.p. 53°C, [α]32D+206°, λmethanolmax. 240nm; ε 3806 litre·mol−1·cm−1) was characterized as a partially reduced derivative of (−)-phyllostine and was found to be a diastereoisomer of the known phytotoxin, (+)-epoxydon. Hence its designation as (+)-iso- or epi-epoxydon. From 1H n.m.r. and c.d. data the stereochemistry of the epoxide ring in (+)-isoepoxydon was determined to be identical with that in (+)-epoxydon (i.e. R,R) but the configuration of the secondary alcohol at C-4 was S rather than R as in (+)-epoxydon. Isoepoxydon (compound UIII) is therefore (4S,5R,6R)-5,6-epoxy-4-hydroxy-2-hydroxymethylcyclohex-2-en-1-one. The boat conformation in which the C-4 hydroxy group is axial is preferred. In the range of 1mm to 5mm, the antibiotic activity of (+)-isoepoxydon against Bacillus subtilis sp. was 56% of that obtained with patulin. Over a period of 1 to 3h, [14C]isoepoxydon was efficiently converted into patulin by a shake culture of the parent strain of P. urticae. The precursor relationship of isoepoxydon to patulin was confirmed by feeding unlabelled isoepoxydon (1mm) to a washed-cell suspension of a mutant (J2) in which, over a period of 3 to 5h, a better than 60% conversion into patulin was attained. The enzymic relationship between isoepoxydon and phyllostine and their positions in the late portion of the patulin biosynthetic pathway are discussed.

scholarly journals Diastereoisomeric analogues of gramicidin S: structure, biological activity and interaction with lipid bilayers

2000 ◽  
Vol 349 (3) ◽  
pp. 747-755 ◽  
Author(s):  
Masood JELOKHANI-NIARAKI ◽  
Leslie H. KONDEJEWSKI ◽  
Susan W. FARMER ◽  
Robert E. W. HANCOCK ◽  
Cyril M. KAY ◽  
...  
Keyword(s):  
Biological Activity ◽  
Lipid Bilayers ◽  
Lipid Membranes ◽  
Cyclic Peptides ◽  
Cyclic Peptide ◽  
Cd Spectra ◽  
Gramicidin S ◽  
Sds Micelles ◽  
Related Approach ◽  
Relationship Of

Analogues of a structurally equivalent version of the antimicrobial decameric cyclic peptide gramicidin S, GS10 [cyclo-(Val-Lys-Leu-D-Tyr-Pro)2], were designed to study the effect of distortion in the β-sheet/β-turn structure of the cyclic peptide on its biological activity. In one approach, the hydrophobic nature of GS10 was conserved, and single amino acids in its backbone were replaced systematically with their corresponding enantiomers to give five diastereoisomeric analogues. In a related approach, a more basic and hydrophilic analogue of GS10 [cyclo-(Lys-Val-Lys-D-Tyr-Pro5-Lys-Leu-Lys-D-Tyr-Pro10)], together with two of its monosubstituted diastereoisomeric analogues (featuring D-Lys1 or D-Val2 respectively), were synthesized. CD spectra were measured in a variety of environments, i.e. aqueous, aqueous trifluoroethanol and those containing SDS micelles or phospholipid vesicles. In comparison with GS10 spectra, CD spectra of both groups of analogues in these environments exhibited structural distortion. Moreover, compared with GS10, antimicrobial and haemolytic activities of the analogues were drastically decreased, implying the existence of a threshold minimum amphipathicity for effective biological activity. However, in both groups of analogues, there was a correlation between amphipathicity and antimicrobial and haemolytic activities. In the second group of analogues, both electrostatic and hydrophobic factors were related to their antimicrobial and haemolytic activities. In order to gain an insight into the nature of the biological activity of the two classes of cyclic peptides, the relationship of their structure to interaction with lipid membranes, and the implied mechanisms, were analysed in some detail in the present study.

Structure-activity relationship of gramicidin S analogues on membrane permeability

1987 ◽  
Vol 899 (2) ◽  
pp. 159-170 ◽  
Author(s):  
Takashi Katsu ◽  
Hideki Kobayashi ◽  
Takashi Hirota ◽  
Yuzaburo Fujita ◽  
Kazuki Sato ◽  
...  
Keyword(s):  
Membrane Permeability ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Gramicidin S ◽  
Structure Activity ◽  
Relationship Of

Design and Synthesis of Gramicidin S Analogs with High Antibiotic Activity

2013 ◽  
Vol 86 (1) ◽  
pp. 112-120 ◽  
Author(s):  
Kazuki Sato ◽  
Yoko Yamaguchi ◽  
Ukon Nagai
Keyword(s):  
Antibiotic Activity ◽  
Design And Synthesis ◽  
Gramicidin S

Fatty acyl-gramicidin S derivatives with both high antibiotic activity and low hemolytic activity

2012 ◽  
Vol 22 (1) ◽  
pp. 106-109 ◽  
Author(s):  
Makoto Tamaki ◽  
Kenta Fujinuma ◽  
Takuji Harada ◽  
Kazumasa Takanashi ◽  
Mitsuno Shindo ◽  
...  
Keyword(s):  
Hemolytic Activity ◽  
Fatty Acyl ◽  
Antibiotic Activity ◽  
Gramicidin S

scholarly journals Specificity of combination between mucopeptide precursors and vancomycin or ristocetin

1969 ◽  
Vol 111 (2) ◽  
pp. 195-205 ◽  
Author(s):  
H R Perkins
Keyword(s):  
Complex Formation ◽  
Dissociation Constants ◽  
Antibiotic Activity ◽  
Differential Absorption ◽  
Ultraviolet Spectra ◽  
Antibiotic Action ◽  
Relationship Of ◽  
The Relationship

Vancomycin and ristocetin formed complexes on being mixed with mucopeptide precursors from various bacteria, as shown by chromatography, electrophoresis and differential ultraviolet spectra. Equimolar proportions of antibiotic and peptide were present. The specificity of the reaction was studied and the smallest molecule found to react was acetyl-d-alanyl-d-alanine. This C-terminal dipeptide sequence must be present for complex-formation; change of configuration or esterification prevented it. Modified vancomycins that retained antibiotic activity also combined with appropriate peptides. The dissociation constants of the more stable complexes were estimated from the differential-absorption results. The relationship of complex-formation to antibiotic action is discussed. Penicillin, supposed to be an analogue of acyl-d-alanyl-d-alanine, also modified the spectrum of vancomycin; so, too, did sodium benzylpenicilloate.

scholarly journals Polycationic Gramicidin S Analogues with Both High Antibiotic Activity and Very Low Hemolytic Activity

2012 ◽  
Vol 60 (9) ◽  
pp. 1134-1138 ◽  
Author(s):  
Makoto Tamaki ◽  
Takuji Harada ◽  
Kenta Fujinuma ◽  
Kazumasa Takanashi ◽  
Mitsuno Shindo ◽  
...  
Keyword(s):  
Hemolytic Activity ◽  
Antibiotic Activity ◽  
Gramicidin S

scholarly journals Novel Cycloundecapeptides Related to Gramicidin S with Both High Antibiotic Activity and Low Hemolytic Activity

2011 ◽  
Vol 59 (12) ◽  
pp. 1481-1484 ◽  
Author(s):  
Makoto Tamaki ◽  
Kazumasa Takanashi ◽  
Takuji Harada ◽  
Kenta Fujinuma ◽  
Mitsuno Shindo ◽  
...  
Keyword(s):  
Hemolytic Activity ◽  
Antibiotic Activity ◽  
Gramicidin S
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