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MedKoo Cat#: 463540 | Name: Edeine A

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Edeine A is an analogue of a basic polypeptide antibiotic produced by Bacillus brevis.

Chemical Structure

Edeine A
Edeine A
CAS#52452-77-4

Theoretical Analysis

MedKoo Cat#: 463540

Name: Edeine A

CAS#: 52452-77-4

Chemical Formula: C33H58N10O10

Exact Mass: 754.4337

Molecular Weight: 754.89

Elemental Analysis: C, 52.51; H, 7.74; N, 18.56; O, 21.19

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Edeine A; Edeine A1; Edeine-A1; Edeine-A;
IUPAC/Chemical Name
6-amino-2-(3-amino-2-(3-(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
InChi Key
HENXXJCYASTLGZ-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
NCCCCNCCCNC(CNC(CC(C(CCCC(C(O)=O)NC(C(NC(C(CNC(CC(c1ccc(O)cc1)N)=O)O)=O)CN)=O)N)O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 754.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Johnson ET, Bowman MJ, Dunlap CA. Brevibacillus fortis NRS-1210 produces edeines that inhibit the in vitro growth of conidia and chlamydospores of the onion pathogen Fusarium oxysporum f. sp. cepae. Antonie Van Leeuwenhoek. 2020 Jul;113(7):973-987. doi: 10.1007/s10482-020-01404-7. Epub 2020 Apr 11. PMID: 32279200. 2: Garlapati S, Wang CC. Giardiavirus internal ribosome entry site has an apparently unique mechanism of initiating translation. PLoS One. 2009 Oct 14;4(10):e7435. doi: 10.1371/journal.pone.0007435. PMID: 19826476; PMCID: PMC2757703. 3: Czajgucki Z, Andruszkiewicz R, Kamysz W. Structure activity relationship studies on the antimicrobial activity of novel edeine A and D analogues. J Pept Sci. 2006 Oct;12(10):653-62. doi: 10.1002/psc.775. PMID: 16847816. 4: Thompson SR, Gulyas KD, Sarnow P. Internal initiation in Saccharomyces cerevisiae mediated by an initiator tRNA/eIF2-independent internal ribosome entry site element. Proc Natl Acad Sci U S A. 2001 Nov 6;98(23):12972-7. doi: 10.1073/pnas.241286698. Epub 2001 Oct 30. PMID: 11687653; PMCID: PMC60809. 5: Shimotohno KW, Iida J, Endo T. A new enzyme, edeine B1 amidinohydrolase, from Bacillus brevis TT02-8. Purification and determination of the N-terminal amino acid sequence. J Antibiot (Tokyo). 1999 Apr;52(4):407-11. doi: 10.7164/antibiotics.52.407. PMID: 10395276. 6: Kurylo-Borowska Z, Heaney-Kieras J. Edeine A, edeine B, and guanidospermidine. Methods Enzymol. 1983;94:441-51. doi: 10.1016/s0076-6879(83)94080-6. PMID: 6621399. 7: Wojciechowska H, Zgoda W, Borowski E. The selectivity of amino acid and peptide amidination with O-methylisourea. Acta Biochim Pol. 1982;29(3-4):197-204. PMID: 7158170. 8: Mazerski J, Wojciechowska H, Zgoda W, Woynarowska B, Borowski E. Esters and amides of edeine A. J Antibiot (Tokyo). 1981 Jan;34(1):28-33. doi: 10.7164/antibiotics.34.28. PMID: 7251506. 9: Heaney-Kieras J, Kurylo-Borowska Z. Tatumine, a peptide from Bacillus brevis Vm4-572-403. J Antibiot (Tokyo). 1980 Apr;33(4):359-63. doi: 10.7164/antibiotics.33.359. PMID: 7410204. 10: Kurylo-Borowska Z, Heaney-Kieras J. The uptake and subcellular localization of the peptide antibiotic edeine A in HeLa cells in suspension culture. Exp Cell Res. 1979 Dec;124(2):371-9. doi: 10.1016/0014-4827(79)90212-x. PMID: 510421. 11: Odon OW, Kramer G, Henderson AB, Pinphanichakarn P, Hardesty B. GTP hydrolysis during methionyl-tRNAf binding to 40 S ribosomal subunits and the site of edeine inhibition. J Biol Chem. 1978 Mar 25;253(6):1807-16. PMID: 246033. 12: Kurylo-Borowska Z. Biosynthesis of edeine: II. Localization of edeine synthetase within Bacillus brevis Vm4. Biochim Biophys Acta. 1975 Jul 14;399(1):31-41. PMID: 1148278. 13: Kurylo-Borowska Z, Sedkowska J. Biosynthesis of edeine. Fractionation and characterization of enzymes responsible for biosynthesis of edeine A and B. Biochim Biophys Acta. 1974 May 10;351(1):42-56. PMID: 4834681. 14: Hettinger TP, Craig LC. Edeine. II. The composition of the antibiotic peptide edeine A. Biochemistry. 1968 Dec;7(12):4147-53. doi: 10.1021/bi00852a001. PMID: 5700644. 15: Borowski E, Chmara H. The antibiotic edeine. 8. The mode of action of edeine A and B. Acta Microbiol Pol. 1968;17(3):241-8. PMID: 4177303. 16: Chmara H, Borowski E. Antibiotic edeine. VII. Biological activity of edeine A and B. Acta Microbiol Pol. 1968;17(1):59-66. PMID: 4172274.