Edeine D

• CAT Number: I026708
• CAS Number: 40627-96-1
• Molecular Formula: C33H58N10O9
• Molecular Weight: 738.88
• Purity: 98%
• Synonyms: Edeine D
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (2R,6S,7R)-6-amino-2-[[(2S)-3-amino-2-[[(3R)-3-amino-3-hydroxypropanoyl]-[(2S)-3-amino-2-phenylpropanoyl]amino]propanoyl]amino]-9-[[2-[3-(4-aminobutylamino)propylamino]acetyl]amino]-7-hydroxy-9-oxononanoic acid
• InChI: InChI=1S/C33H58N10O9/c34-12-4-5-13-39-14-7-15-40-20-29(47)42-28(46)16-26(44)23(37)10-6-11-24(33(51)52)41-31(49)25(19-36)43(30(48)17-27(38)45)32(50)22(18-35)21-8-2-1-3-9-21/h1-3,8-9,22-27,39-40,44-45H,4-7,10-20,34-38H2,(H,41,49)(H,51,52)(H,42,46,47)/t22-,23+,24-,25+,26-,27-/m1/s1
• InChIKey: FPJBIRIVZPUIOL-DDURVGIBSA-N
• SMILES: C1=CC=C(C=C1)[C@@H](CN)C(=O)N([C@@H](CN)C(=O)N[C@H](CCC[C@@H]([C@@H](CC(=O)NC(=O)CNCCCNCCCCN)O)N)C(=O)O)C(=O)C[C@H](N)O

Edeine D（Cat No.:I026708）is a natural product and a potent antibiotic belonging to the edeine family of compounds. It is primarily isolated from Streptomyces species and has been studied for its antimicrobial activity, particularly against Gram-positive bacteria. Edeine D functions by inhibiting protein synthesis through binding to the bacterial ribosome, which prevents the elongation of peptides. This mechanism makes it effective in combating bacterial infections. Due to its powerful antibacterial properties, it is of interest in developing new antibiotics, particularly for drug-resistant bacterial strains, though its clinical use is still under investigation.

Reference

1: Mao H, Jeong H, Yang J, Ha HJ, Yang JW. Preparation of Chiral Contiguous Epoxyaziridines and Their Regioselective Ring-Opening for Drug Syntheses. Chemistry. 2018 Feb 16;24(10):2370-2374. doi: 10.1002/chem.201706161. Epub 2018 Jan 25. PubMed PMID: 29314353.
2: 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. PubMed PMID: 16847816.
3: Gumieniak J, Andruszkiewicz R, Czerwiński A, Grzybowska J, Borowski E. Synthesis of the decarboxy analog of edeine D. J Antibiot (Tokyo). 1983 Sep;36(9):1239-41. PubMed PMID: 6415032.
4: Czerwiński A, Wojciechowska H, Andruszkiewicz R, Grzybowska J, Gumieniak J, Borowski E. Total synthesis of edeine D. J Antibiot (Tokyo). 1983 Aug;36(8):1001-6. PubMed PMID: 6415028.
5: Wojciechowska H, Zgoda W, Borowski E, Dziegielewski K, Ulikowski S. The antibiotic edeine. XII. Isolation and structure of edeine F. J Antibiot (Tokyo). 1983 Jul;36(7):793-8. PubMed PMID: 6615592.
6: Wojciechowska H, Ciarkowski J, Chmara H, Borowski E. The antibiotic edeine. IX. The isolation and the composition of edeine D. Experientia. 1972 Dec 15;28(12):1423-4. PubMed PMID: 4654193.