Edeine A1
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| Category | Antibiotics |
| Catalog number | BBF-01197 |
| CAS | 27656-72-0 |
| Molecular Formula | C33H58N10O10 |
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Description
It is produced by the strain of Bacillus brevis Vm4. It can inhibit DNA replication and protein biosynthesis, and has anti-gram-positive bacteria, gram-negative bacteria, fungi and yeast activities.
Specification
| Synonyms | Glycinamide, N8-[(3S)-3-(4-hydroxyphenyl)-b-alanyl-(2S)-2-hydroxy-b-alanyl-3-amino-L-alanyl]-(3R,4S,8R)-4,8-diamino-8-carboxy-3-hydroxyoctanoyl-N-[3-[(4-aminobutyl)amino]propyl]-(9CI); NSC 663297 |
| IUPAC Name | (2R,6S,7R)-6-amino-2-((S)-3-amino-2-((S)-3-((S)-3-amino-3-(4-hydroxyphenyl)propanamido)-2-hydroxypropanamido)propanamido)-9-((2-((3-((4-aminobutyl)amino)propyl)amino)-2-oxoethyl)amino)-7-hydroxy-9-oxononanoic acid |
| Canonical SMILES | C1=CC(=CC=C1C(CC(=O)NCC(C(=O)NC(CN)C(=O)NC(CCCC(C(CC(=O)NCC(=O)NCCCNCCCCN)O)N)C(=O)O)O)N)O |
| InChI | InChI=1S/C33H58N10O10/c34-11-1-2-12-38-13-4-14-39-30(49)19-41-29(48)16-26(45)22(36)5-3-6-24(33(52)53)42-31(50)25(17-35)43-32(51)27(46)18-40-28(47)15-23(37)20-7-9-21(44)10-8-20/h7-10,22-27,38,44-46H,1-6,11-19,34-37H2,(H,39,49)(H,40,47)(H,41,48)(H,42,50)(H,43,51)(H,52,53) |
| InChI Key | HENXXJCYASTLGZ-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Fungi; Yeast |
| Boiling Point | 1240.3 °C at 760 mmHg |
| Density | 1.304 g/cm3 |
| Solubility | Soluble in Water, Methanol |
Reference Reading
1. GTP hydrolysis during methionyl-tRNAf binding to 40 S ribosomal subunits and the site of edeine inhibition
O W Odon, G Kramer, A B Henderson, P Pinphanichakarn, B Hardesty J Biol Chem. 1978 Mar 25;253(6):1807-16.
Three lines of evidence are presented indicating that GTP hydrolysis associated with eukaryotic peptide initiation occurs in the absence of 60 S subunits when methionyl-tRNAf is bound to 40 S ribosomal subunits. An enzyme fraction required for binding of methionyl-tRNAf to 40 S subunits and peptide initiation, tentatively equated with eIF-(4 + 5), has GTPase activity and appears to be responsible for hydrolysis of GTP in the methionyl-tRNAf.eIF-2.GTP complex. Direct analysis of the methionyl-tRNAf.40 S complex formed with with eIF-2 and [8-3H] guanine, [gamma-32P]GTP reveals bound guanine but not gamma-phosphate. Edeine, a peptide antibiotic containing spermidine and beta-tyrosine residues at its COOH terminus and NH2 terminus, respectively, blocks peptide initiation and interferes with binding of methionyl-tRNAf to 40 S ribosomal subunits. Inhibition of binding is observed when the eIF-2-mediated binding reaction is carried out with GTP but not with guanosine 5'-(beta,gamma-methylene)triphosphate or guanosine 5'-(beta,gamma-imido)triphosphate. Edeine was labeled by iodination and shown to bind with high affinity to 40 S but not to 60 S ribosomal subunits. It is suggested that edeine blocks a specific site on the 40 S ribosomal subunit to which a segment of the methionyl-tRNAf molecule is bound during the course of the initiation reaction sequence.
2. Esters and amides of edeine A
J Mazerski, H Wojciechowska, W Zgoda, B Woynarowska, E Borowski J Antibiot (Tokyo). 1981 Jan;34(1):28-33. doi: 10.7164/antibiotics.34.28.
Methods for the synthesis of esters and amides of edeine A were developed and a number of derivatives of this type was obtained and characterized. The antimicrobial activities of the derivatives are comparable to the activity of the native antibiotic and indicate that the presence of free carboxyl group in edeine is not essential for its biological assay.
3. Structure activity relationship studies on the antimicrobial activity of novel edeine A and D analogues
Zbigniew Czajgucki, Ryszard Andruszkiewicz, Wojciech Kamysz J Pept Sci. 2006 Oct;12(10):653-62. doi: 10.1002/psc.775.
Edeines are pentapeptide amide antibiotics composed of four nonprotein amino acids, glycine, and polyamine. They exhibit antimicrobial and immunosuppressive activities and are universal inhibitors of translation. Moreover, it was proven that the free ionizable carboxy group in the (2R, 6S, 7R)-2,6-diamino-7-hydroxyazelaic acid moiety is not essential for biological activity of these compounds. In this paper we describe the synthesis of four novel edeine A and D analogues in which the above-mentioned acid residue was replaced with the (3R, 4S)- or (3S, 4S)-4,5-diamino-3-hydroxypentanoic acid moiety. In one compound we also introduced into molecule the 3-N,N-dimethyl derivative of (S)-2,3-diaminopropanoic acid to prevent the transpeptidation process, which results in the loss of biological activity of alpha-isomers of edeines. All peptides were synthesized applying the active ester and azide methods and on the basis of the coupling of suitable N-terminal tripeptides with proper C-terminal dipeptide amides. The activities of the newly obtained edeine analogues against selected strains of bacteria and fungi are also presented.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
