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MedKoo Cat#: 461687 | Name: Amicetin

Description:

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

Amicetin is an antibacterial and antiviral agent, belongs to a group of disaccharide nucleoside antibiotics featuring an α-(1→4)-glycoside bond in the disaccharide moiety.

Chemical Structure

Amicetin
Amicetin
CAS#17650-86-1

Theoretical Analysis

MedKoo Cat#: 461687

Name: Amicetin

CAS#: 17650-86-1

Chemical Formula: C29H42N6O9

Exact Mass: 618.3013

Molecular Weight: 618.68

Elemental Analysis: C, 56.30; H, 6.84; N, 13.58; O, 23.27

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
Amicetin; Amicetin-A; Amicetin A; D-13; D 13; D13; Sacromycin; U-4761; U 4761; U4761;
IUPAC/Chemical Name
4-(2-amino-3-hydroxy-2-methylpropanamido)-N-(1-((2R,5S,6R)-5-(((2R,3R,4S,5S,6R)-5-(dimethylamino)-3,4-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide
InChi Key
HDNVYHWHCVTDIV-AUHWTNQGSA-N
InChi Code
InChI=1S/C29H42N6O9/c1-15-19(44-26-24(38)23(37)22(34(4)5)16(2)43-26)10-11-21(42-15)35-13-12-20(33-28(35)41)32-25(39)17-6-8-18(9-7-17)31-27(40)29(3,30)14-36/h6-9,12-13,15-16,19,21-24,26,36-38H,10-11,14,30H2,1-5H3,(H,31,40)(H,32,33,39,41)/t15-,16-,19+,21-,22-,23+,24-,26-,29?/m1/s1
SMILES Code
OCC(C)(N)C(NC1=CC=C(C(NC(C=CN2[C@H]3CC[C@@H]([C@@H](C)O3)O[C@@H]4[C@@H]([C@H]([C@H](N(C)C)[C@@H](C)O4)O)O)=NC2=O)=O)C=C1)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 618.68 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: Zhang G, Zhang H, Li S, Xiao J, Zhang G, Zhu Y, Niu S, Ju J, Zhang C. Characterization of the amicetin biosynthesis gene cluster from Streptomyces vinaceusdrappus NRRL 2363 implicates two alternative strategies for amide bond formation. Appl Environ Microbiol. 2012 Apr;78(7):2393-401. doi: 10.1128/AEM.07185-11. Epub 2012 Jan 20. PubMed PMID: 22267658; PubMed Central PMCID: PMC3302616. 2: Chen R, Zhang H, Zhang G, Li S, Zhang G, Zhu Y, Liu J, Zhang C. Characterizing amosamine biosynthesis in amicetin reveals AmiG as a reversible retaining glycosyltransferase. J Am Chem Soc. 2013 Aug 21;135(33):12152-5. doi: 10.1021/ja401016e. Epub 2013 Aug 9. PubMed PMID: 23919735. 3: Hu T, Zhang G, Zhu Y, Li S, Zhang H, Zhang G, Yang X, Ju J, Zhang C. [Cloning, expression and characterization of the nucleotidylyltransferase gene-amiE in amicetin biosynthesis]. Wei Sheng Wu Xue Bao. 2012 Feb 4;52(2):214-20. Chinese. PubMed PMID: 22587000. 4: Bu YY, Yamazaki H, Ukai K, Namikoshi M. Anti-mycobacterial nucleoside antibiotics from a marine-derived Streptomyces sp. TPU1236A. Mar Drugs. 2014 Dec 17;12(12):6102-12. doi: 10.3390/md12126102. PubMed PMID: 25522318; PubMed Central PMCID: PMC4278220. 5: Shammas C, Donarski JA, Ramesh V. NMR structure of the peptidyl transferase RNA inhibitor antibiotic amicetin. Magn Reson Chem. 2007 Feb;45(2):133-41. PubMed PMID: 17146803. 6: Niu G, Tan H. Nucleoside antibiotics: biosynthesis, regulation, and biotechnology. Trends Microbiol. 2015 Feb;23(2):110-9. doi: 10.1016/j.tim.2014.10.007. Epub 2014 Nov 13. Review. PubMed PMID: 25468791. 7: Donarski J, Shammas C, Banks R, Ramesh V. NMR and molecular modelling studies of the binding of amicetin antibiotic to conserved secondary structural motifs of 23S ribosomal RNAs. J Antibiot (Tokyo). 2006 Mar;59(3):177-83. PubMed PMID: 16724458. 8: Kim UJ, Ambulos NP Jr, Duvall EJ, Lorton MA, Lovett PS. Site in the cat-86 regulatory leader that permits amicetin to induce expression of the gene. J Bacteriol. 1988 Jul;170(7):2933-8. PubMed PMID: 3133355; PubMed Central PMCID: PMC211231. 9: Itoh J, Miyadoh S. SF2457, a new antibiotic related to amicetin. J Antibiot (Tokyo). 1992 Jun;45(6):846-53. PubMed PMID: 1500349. 10: Gu Z, Lovett PS. A gratuitous inducer of cat-86, amicetin, inhibits bacterial peptidyl transferase. J Bacteriol. 1995 Jun;177(12):3616-8. PubMed PMID: 7768878; PubMed Central PMCID: PMC177074. 11: Ambulos NP Jr, Duvall EJ, Lovett PS. Analysis of the regulatory sequences needed for induction of the chloramphenicol acetyltransferase gene cat-86 by chloramphenicol and amicetin. J Bacteriol. 1986 Sep;167(3):842-9. PubMed PMID: 3462183; PubMed Central PMCID: PMC215950. 12: Duvall EJ, Mongkolsuk S, Kim UJ, Lovett PS, Henkin TM, Chambliss GH. Induction of the chloramphenicol acetyltransferase gene cat-86 through the action of the ribosomal antibiotic amicetin: involvement of a Bacillus subtilis ribosomal component in cat induction. J Bacteriol. 1985 Feb;161(2):665-72. PubMed PMID: 3918021; PubMed Central PMCID: PMC214934. 13: Leviev IG, Rodriguez-Fonseca C, Phan H, Garrett RA, Heilek G, Noller HF, Mankin AS. A conserved secondary structural motif in 23S rRNA defines the site of interaction of amicetin, a universal inhibitor of peptide bond formation. EMBO J. 1994 Apr 1;13(7):1682-6. PubMed PMID: 8157007; PubMed Central PMCID: PMC394999. 14: SENSI P, GRECO AM, GALLO GG, ROLLAND G. Isolation and structure determination of a new amicetin-like antibiotic: amicetin B. Antibiot Chemother (Northfield). 1957 Dec;7(12):645-52. PubMed PMID: 24544597. 15: BURCHENAL JH, YUCEOGLU M, DAGG MK, STOCK CC. Leukemia. VI. Effect of amicetin on transplanted mouse leukemia. Proc Soc Exp Biol Med. 1954 Aug-Sep;86(4):891-3. PubMed PMID: 13204387. 16: TAN CT, BURCHENAL JH. Clinical studies with amicetin. Antibiotic Med Clin Ther (New York). 1956 Jul;3(2):126-31. PubMed PMID: 13340692. 17: Konstantinova NV, Fedorova GB, Borisova VN, Shapovalova SP, Malkova IV. [Isolation and identification of the antibiotics amicetin and nebramycin formed by a Streptomyces coeruleoaurantiacus 4009 culture]. Antibiotiki. 1982 Jun;27(6):403-9. Russian. PubMed PMID: 7114825. 18: Theocharis DA, Kalpaxis DL, Coutsogeorgopoulos C. Aminoacylaminonucleoside inhibitors of protein synthesis. A new approach for evaluating their potency. Eur J Biochem. 1986 Sep 15;159(3):479-83. PubMed PMID: 3758072. 19: Renis HE. In vitro antiviral activity of amicetin and its derivatives. Antimicrob Agents Chemother (Bethesda). 1965;5:567-73. PubMed PMID: 5883473. 20: HINUMA Y, KUROYA M, YAJIMA T, ISHIHARA K, HAMADA S, WATANABE K, KIKUCHI K. An amicetin (sacromycin) from Streptomyces sp. No. 5223. Studies on Streptomyces antibiotics. XXXVI. J Antibiot (Tokyo). 1955 Nov;8(5):148-52. PubMed PMID: 13306673.