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MedKoo Cat#: 598177 | Name: Pulvomycin

Description:

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

Pulvomycin is an inhibitor of protein biosynthesis preventing ternary complex formation between elongation factor Tu, GTP, and aminoacyl-tRNA.

Chemical Structure

Pulvomycin
Pulvomycin
CAS#11006-66-9

Theoretical Analysis

MedKoo Cat#: 598177

Name: Pulvomycin

CAS#: 11006-66-9

Chemical Formula: C47H66O13

Exact Mass: 838.4503

Molecular Weight: 839.03

Elemental Analysis: C, 67.28; H, 7.93; O, 24.79

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
Pulvomycin; Antibiotic 1063Z;
IUPAC/Chemical Name
(4E,7Z,9Z,11Z,15Z,17E,19Z)-22-((6E,8E,10E)-3,12-dihydroxy-13-(((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-methyl-5-oxotetradeca-6,8,10-trien-2-yl)-6,14-dihydroxy-5,8,12-trimethyloxacyclodocosa-4,7,9,11,15,17,19-heptaene-2,13-dione
InChi Key
FXSFWUNCIOIMAC-CFJLSIFESA-N
InChi Code
InChI=1S/C47H66O13/c1-29-20-19-21-31(3)42(53)38(50)24-17-11-10-12-18-25-40(60-41(52)27-26-30(2)39(51)28-29)33(5)43(54)32(4)36(48)22-15-13-14-16-23-37(49)34(6)58-47-46(57-9)44(55)45(56-8)35(7)59-47/h10-24,26,28,32-35,37-40,43-47,49-51,54-55H,25,27H2,1-9H3/b11-10+,14-13+,18-12-,20-19-,22-15+,23-16+,24-17-,29-28-,30-26+,31-21-/t32?,33?,34?,35-,37?,38?,39?,40?,43?,44+,45+,46-,47-/m1/s1
SMILES Code
O=C(C/C=C(C)/C(O)/C=C(C)\C=C/C=C1/C)OC(C(C)C(O)C(C)C(/C=C/C=C/C=C/C(O)C(O[C@H]2[C@@H]([C@H]([C@H]([C@@H](C)O2)OC)O)OC)C)=O)C/C=C\C=C\C=C/C(O)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 839.03 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: Börding S, Bach T. An enantioselective synthesis of the C24-C40 fragment of (-)-pulvomycin. Chem Commun (Camb). 2014 May 18;50(38):4901-3. doi: 10.1039/c4cc01338g. PubMed PMID: 24691561. 2: Martucci NM, Lamberti A, Arcari P, Masullo M. The eubacterial protein synthesis inhibitor pulvomycin interacts with archaeal elongation factor 1α from Sulfolobus solfataricus. Biochimie. 2012 Feb;94(2):503-9. doi: 10.1016/j.biochi.2011.08.019. Epub 2011 Sep 10. PubMed PMID: 21924318. 3: Cammarano P, Teichner A, Chinali G, Londei P, de Rosa M, Gambacorta A, Nicolaus B. Archaebacterial elongation factor Tu insensitive to pulvomycin and kirromycin. FEBS Lett. 1982 Nov 8;148(2):255-9. PubMed PMID: 6759168. 4: Landini P, Bandera M, Soffientini A, Goldstein BP. Sensitivity of elongation factor Tu (EF-Tu) from different bacterial species to the antibiotics efrotomycin, pulvomycin and MDL 62879. J Gen Microbiol. 1993 Apr;139(4):769-74. PubMed PMID: 8515234. 5: Parmeggiani A, Krab IM, Okamura S, Nielsen RC, Nyborg J, Nissen P. Structural basis of the action of pulvomycin and GE2270 A on elongation factor Tu. Biochemistry. 2006 Jun 6;45(22):6846-57. PubMed PMID: 16734421. 6: Zeef LA, Bosch L, Anborgh PH, Cetin R, Parmeggiani A, Hilgenfeld R. Pulvomycin-resistant mutants of E.coli elongation factor Tu. EMBO J. 1994 Nov 1;13(21):5113-20. PubMed PMID: 7957075; PubMed Central PMCID: PMC395458. 7: Anborgh PH, Okamura S, Parmeggiani A. Effects of the antibiotic pulvomycin on the elongation factor Tu-dependent reactions. Comparison with other antibiotics. Biochemistry. 2004 Dec 14;43(49):15550-6. PubMed PMID: 15581367. 8: ZIEF M, WOODSIDE R, SCHMITZ H. Pulvomycin. Antibiot Chemother (Northfield). 1957 Jul;7(7):384-6. PubMed PMID: 24544485. 9: Assmann D, Wolf H. Pulvomycin, an inhibitor of prokaryotic protein biosynthesis. Arch Microbiol. 1979 Mar 12;120(3):297-9. PubMed PMID: 375861. 10: Boon K, Krab I, Parmeggiani A, Bosch L, Kraal B. Substitution of Arg230 and Arg233 in Escherichia coli elongation factor Tu strongly enhances its pulvomycin resistance. Eur J Biochem. 1995 Feb 1;227(3):816-22. PubMed PMID: 7867642. 11: Wolf H, Assmann D, Fischer E. Pulvomycin, an inhibitor of protein biosynthesis preventing ternary complex formation between elongation factor Tu, GTP, and aminoacyl-tRNA. Proc Natl Acad Sci U S A. 1978 Nov;75(11):5324-8. PubMed PMID: 364475; PubMed Central PMCID: PMC392955. 12: Möhrle VG, Tieleman LN, Kraal B. Elongation factor Tu1 of the antibiotic GE2270A producer Planobispora rosea has an unexpected resistance profile against EF-Tu targeted antibiotics. Biochem Biophys Res Commun. 1997 Jan 13;230(2):320-6. PubMed PMID: 9016775. 13: Schwartz JL, Tishler M, Arison BH, Shafer HM, Omura S. Identification of mycolutein and pulvomycin as aureothin and labilomycin respectively. J Antibiot (Tokyo). 1976 Mar;29(3):236-41. PubMed PMID: 770405. 14: Glöckner C, Wörner W, Wolf H. Kirromycin-resistant elongation factor Tu from pulvomycin-producing wild-type of Streptoverticillium mobaraense. Biochem Biophys Res Commun. 1982 Aug;107(3):959-65. PubMed PMID: 6890351. 15: Kraal B, Zeef LA, Mesters JR, Boon K, Vorstenbosch EL, Bosch L, Anborgh PH, Parmeggiani A, Hilgenfeld R. Antibiotic resistance mechanisms of mutant EF-Tu species in Escherichia coli. Biochem Cell Biol. 1995 Nov-Dec;73(11-12):1167-77. Review. PubMed PMID: 8722034. 16: Pingoud A, Block W, Urbanke C, Wolf H. The antibiotics kirromycin and pulvomycin bind to different sites on the elongation factor Tu from Escherichia coli. Eur J Biochem. 1982 Apr 1;123(2):261-5. PubMed PMID: 6122571. 17: Wörner W, Wolf H. Kirromycin-resistant elongation factor Tu from wild-type of Lactobacillus brevis. FEBS Lett. 1982 Sep 20;146(2):322-6. PubMed PMID: 6890473. 18: McKenzie NL, Thaker M, Koteva K, Hughes DW, Wright GD, Nodwell JR. Induction of antimicrobial activities in heterologous streptomycetes using alleles of the Streptomyces coelicolor gene absA1. J Antibiot (Tokyo). 2010 Apr;63(4):177-82. doi: 10.1038/ja.2010.13. Epub 2010 Mar 12. PubMed PMID: 20224601. 19: Schmid B, Anke T, Wolf H. Action of pulvomycin and kirromycin on eukaryotic cells. FEBS Lett. 1978 Dec 1;96(1):189-91. PubMed PMID: 729785. 20: Krásný L, Mesters JR, Tieleman LN, Kraal B, Fucík V, Hilgenfeld R, Jonák J. Structure and expression of elongation factor Tu from Bacillus stearothermophilus. J Mol Biol. 1998 Oct 23;283(2):371-81. PubMed PMID: 9769211.