MedKoo Cat#: 592800 | Name: Amphomycin
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Description:

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

Amphomycin inhibits mannosylphosphoryldolichol synthesis by forming a complex with dolichylmonophosphate.

Chemical Structure

Amphomycin
Amphomycin
CAS#1402-82-0

Theoretical Analysis

MedKoo Cat#: 592800

Name: Amphomycin

CAS#: 1402-82-0

Chemical Formula: C58H91N13O20

Exact Mass: 1289.6503

Molecular Weight: 1290.44

Elemental Analysis: C, 53.98; H, 7.11; N, 14.11; O, 24.80

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1mg USD 585.00 2 Weeks
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Related CAS #
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Synonym
Amphomycin
IUPAC/Chemical Name
2,2'-((6S,9R,15S,21S,24S,26aR,33S,34R,36aS)-9-((R)-1-aminoethyl)-33-((2S)-3-carboxy-2-((Z)-10-methyldodec-3-enamido)propanamido)-24-((S)-1-carboxyethyl)-6-isopropyl-34-methyl-5,8,11,14,17,20,23,26,32,36-decaoxotetratriacontahydro-1H,5H-pyrido[1,2-a]pyrrolo[1,2-y][1,4,7,10,13,16,19,22,25,28]decaazacyclohentriacontine-15,21-diyl)diacetic acid
InChi Key
WAFOSUDOWLQGBG-NUZIGYSUSA-N
InChi Code
InChI=1S/C58H91N13O20/c1-8-30(4)18-13-11-9-10-12-14-21-39(72)63-36(26-44(79)80)51(83)69-48-33(7)62-52(84)38-20-17-23-71(38)56(88)45(29(2)3)67-55(87)47(32(6)59)66-41(74)28-61-49(81)34(24-42(75)76)64-40(73)27-60-50(82)35(25-43(77)78)65-54(86)46(31(5)58(90)91)68-53(85)37-19-15-16-22-70(37)57(48)89/h12,14,29-38,45-48H,8-11,13,15-28,59H2,1-7H3,(H,60,82)(H,61,81)(H,62,84)(H,63,72)(H,64,73)(H,65,86)(H,66,74)(H,67,87)(H,68,85)(H,69,83)(H,75,76)(H,77,78)(H,79,80)(H,90,91)/b14-12-/t30?,31-,32+,33+,34-,35-,36-,37+,38-,45-,46-,47+,48-/m0/s1
SMILES Code
O=C(N[C@H](C)[C@@H]1NC([C@@H](NC(C/C=C\CCCCCC(C)CC)=O)CC(O)=O)=O)[C@@](CCC2)([H])N2C([C@H](C(C)C)NC([C@@H]([C@H](N)C)NC(CNC([C@H](CC(O)=O)NC(CNC([C@H](CC(O)=O)NC([C@H]([C@@H](C(O)=O)C)NC([C@](CCCC3)([H])N3C1=O)=O)=O)=O)=O)=O)=O)=O)=O
Appearance
Solid powder
Purity
>95% (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 1,290.44 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: Yang HJ, Huang XZ, Zhang ZL, Wang CX, Zhou J, Huang K, Zhou JM, Zheng W. Two novel amphomycin analogues from Streptomyces canus strain FIM-0916. Nat Prod Res. 2014;28(12):861-7. doi: 10.1080/14786419.2014.886210. Epub 2014 Feb 25. PubMed PMID: 24568288. 2: Singh M, Chang J, Coffman L, Kim SJ. Solid-state NMR characterization of amphomycin effects on peptidoglycan and wall teichoic acid biosyntheses in Staphylococcus aureus. Sci Rep. 2016 Aug 19;6:31757. doi: 10.1038/srep31757. PubMed PMID: 27538449; PubMed Central PMCID: PMC4990924. 3: Banerjee DK, Diaz AM, Campos TM, Grande C, Kozek WJ, Baksi K. Monoclonal antibody to amphomycin. A tool to study the topography of dolichol monophosphate in the membrane. Carbohydr Res. 1992 Dec 15;236:301-13. PubMed PMID: 1291054. 4: Banerjee DK. Amphomycin inhibits mannosylphosphoryldolichol synthesis by forming a complex with dolichylmonophosphate. J Biol Chem. 1989 Feb 5;264(4):2024-8. PubMed PMID: 2464586. 5: HEINEMANN B, KAPLAN MA, MUIR RD, HOOPER IR. Amphomycin, a new antibiotic. Antibiot Chemother (Northfield). 1953 Dec;3(12):1239-42. PubMed PMID: 24542804. 6: PACKCHANIAN A. Chemotherapy of Borrelia anserina infection (spirochetosis) in chicks with amphomycin, kanamycin. telomycin. and tetracycline. Antibiot Chemother (Northfield). 1960 Dec;10:731-9. PubMed PMID: 13731948. 7: CRONK GA, NEUMANN DE. The topical use of amphomycin and amphomycin-neomycin ointments. Antibiotic Med Clin Ther (New York). 1956 Jul;3(2):142-5. PubMed PMID: 13340695. 8: ROBERTS G. TREATMENT OF ACNE VULGARIS WITH A TOPICAL OINTMENT CONTAINING KANAMYCIN, AMPHOMYCIN AND HYDROCORTISONE (KANFOTREX-BRISTOL). Cent Afr J Med. 1964 Jan;10:23-4. PubMed PMID: 14113848. 9: Zhu BC, Drake RR, Schweingruber H, Laine RA. Inhibition of glycosylation by amphomycin and sugar nucleotide analogs PP36 and PP55 indicates that Haloferax volcanii beta-glucosylates both glycoproteins and glycolipids through lipid-linked sugar intermediates: evidence for three novel glycoproteins and a novel sulfated dihexosyl-archaeol glycolipid. Arch Biochem Biophys. 1995 Jun 1;319(2):355-64. PubMed PMID: 7786016. 10: TRINCAO C, DA GRACA MM, DA FONSECA P, NOGUEIRA AR. [Effect of amphomycin on the experimental infection of mice by Trypanosoma rhodesiense]. Bull Soc Pathol Exot Filiales. 1958 Nov-Dec;51(6):893-6. English, French. PubMed PMID: 13662795. 11: REITER HF. [Neomycin-amphomycin ointment in antibiotic local therapy of infected eczema]. Ugeskr Laeger. 1957 Jul 11;119(28):911-4. Danish. PubMed PMID: 13455959. 12: Kang MS, Spencer JP, Elbein AD. Amphomycin inhibition of mannose and GlcNAc incorporation into lipid-linked saccharides. J Biol Chem. 1978 Dec 25;253(24):8860-6. PubMed PMID: 721819. 13: Tanaka H, Oiwa R, Matsukura S, Omura S. Amphomycin inhibits phospho-N-acetylmuramyl-pentapeptide translocase in peptidoglycan synthesis of Bacillus. Biochem Biophys Res Commun. 1979 Feb 14;86(3):902-8. PubMed PMID: 106855. 14: Lakey JH, Maget-Dana R, Ptak M. Conformational change on calcium binding by the lipopeptide antibiotic amphomycin. A C.D. and monolayer study. Biochem Biophys Res Commun. 1988 Jan 15;150(1):384-90. PubMed PMID: 3337719. 15: Gauze GF, Preobrazhenskaia TP, Spiridomova IA, Maksimova TS, Ol'khovatova OL. [New producer of amphomycin-group antibiotics]. Antibiotiki. 1980 Dec;25(12):883-7. Russian. PubMed PMID: 7469391. 16: LUND E. [Amphomycin, a new antibiotic for local application]. Ugeskr Laeger. 1957 Jul 11;119(28):909-11. Danish. PubMed PMID: 13455958. 17: Banerjee DK, Scher MG, Waechter CJ. Amphomycin: effect of the lipopeptide antibiotic on the glycosylation and extraction of dolichyl monophosphate in calf brain membranes. Biochemistry. 1981 Mar 17;20(6):1561-8. PubMed PMID: 7225346. 18: SHORIN VA, SHAPOVALOVA SP. [Comparative studies of antibacterial and therapeutic properties of antibiotics crystallomycin and amphomycin]. Antibiotiki (Mosc). 1959 Jan-Feb;4(1):77-81. Russian. PubMed PMID: 24545232. 19: ROBINSON RC, ROBERTS D. Amphomycin-neomycin-hydrocortisone cream: evaluation of therapeutic properties, patient acceptance, and comparison with currently available similar preparations. Antibiot Chemother (Northfield). 1962 Jan;12:17-21. PubMed PMID: 14492937. 20: Vincent JL, De Backer D. Saline versus balanced solutions: are clinical trials comparing two crystalloid solutions really needed? Crit Care. 2016 Aug 11;20(1):250. doi: 10.1186/s13054-016-1435-x. PubMed PMID: 27511049; PubMed Central PMCID: PMC5050722.