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MedKoo Cat#: 462870 | Name: Paulomycin

Description:

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

Paulomycin is an antibiotic that derives from Streptomyces paulus. It appears to be similar to senfolomycin and proceomycin but seems to have more nitrogen and sulfur.

Chemical Structure

Paulomycin
Paulomycin
CAS#59794-18-2

Theoretical Analysis

MedKoo Cat#: 462870

Name: Paulomycin

CAS#: 59794-18-2

Chemical Formula: C27H34N2O15S

Exact Mass: 658.1680

Molecular Weight: 658.63

Elemental Analysis: C, 49.24; H, 5.20; N, 4.25; O, 36.44; S, 4.87

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
Paulomicina; Paulomycine; Paulomycinum; Volonomycin; U-43,120;
IUPAC/Chemical Name
5-((3R,4S,5R,6R)-6-(acetoxymethyl)-3-hydroxy-4-(((2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5-(((Z)-2-isothiocyanatobut-2-enoyl)oxy)tetrahydro-2H-pyran-2-yl)-2-amino-5-hydroxy-3,6-dioxocyclohex-1-ene-1-carboxylic acid
InChi Key
HYYDZRXDSYTIEH-MQTRCCAJSA-N
InChi Code
InChI=1S/C27H34N2O15S/c1-5-12(29-9-45)26(37)44-21-15(8-40-11(3)30)42-24(27(38)7-13(31)18(28)17(23(27)34)25(35)36)20(33)22(21)43-16-6-14(39-4)19(32)10(2)41-16/h5,10,14-16,19-22,24,32-33,38H,6-8,28H2,1-4H3,(H,35,36)/b12-5-/t10-,14-,15-,16-,19+,20-,21-,22+,24?,27?/m1/s1
SMILES Code
CO[C@@H]1C[C@H](O[C@@H]([C@@H]1O)C)O[C@H]2[C@H](C(C3(CC(C(N)=C(C3=O)C(O)=O)=O)O)O[C@@H]([C@H]2OC(/C(N=C=S)=C/C)=O)COC(C)=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 658.63 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 Y, Wang M, Tian J, Liu J, Guo Z, Tang W, Chen Y. Activation of paulomycin production by exogenous γ-butyrolactone signaling molecules in Streptomyces albidoflavus J1074. Appl Microbiol Biotechnol. 2020 Feb;104(4):1695-1705. doi: 10.1007/s00253-019-10329-9. Epub 2020 Jan 3. PMID: 31900559. 2: Kallifidas D, Jiang G, Ding Y, Luesch H. Rational engineering of Streptomyces albus J1074 for the overexpression of secondary metabolite gene clusters. Microb Cell Fact. 2018 Feb 17;17(1):25. doi: 10.1186/s12934-018-0874-2. PMID: 29454348; PMCID: PMC5816538. 3: Hoz JF, Méndez C, Salas JA, Olano C. Novel Bioactive Paulomycin Derivatives Produced by Streptomyces albus J1074. Molecules. 2017 Oct 18;22(10):1758. doi: 10.3390/molecules22101758. PMID: 29057800; PMCID: PMC6151807. 4: Sarmiento-Vizcaíno A, Braña AF, Pérez-Victoria I, Martín J, de Pedro N, Cruz M, Díaz C, Vicente F, Acuña JL, Reyes F, García LA, Blanco G. Paulomycin G, a New Natural Product with Cytotoxic Activity against Tumor Cell Lines Produced by Deep-Sea Sediment Derived Micromonospora matsumotoense M-412 from the Avilés Canyon in the Cantabrian Sea. Mar Drugs. 2017 Aug 28;15(9):271. doi: 10.3390/md15090271. PMID: 28846627; PMCID: PMC5618410. 5: González A, Rodríguez M, Braña AF, Méndez C, Salas JA, Olano C. New insights into paulomycin biosynthesis pathway in Streptomyces albus J1074 and generation of novel derivatives by combinatorial biosynthesis. Microb Cell Fact. 2016 Mar 21;15:56. doi: 10.1186/s12934-016-0452-4. PMID: 27001601; PMCID: PMC4802897. 6: Li J, Wang M, Ding Y, Tang Y, Zhang Z, Chen Y. Involvement of an octose ketoreductase and two acyltransferases in the biosynthesis of paulomycins. Sci Rep. 2016 Feb 15;6:21180. doi: 10.1038/srep21180. PMID: 26877148; PMCID: PMC4753412. 7: Sarmiento-Vizcaíno A, Braña AF, González V, Nava H, Molina A, Llera E, Fiedler HP, Rico JM, García-Flórez L, Acuña JL, García LA, Blanco G. Atmospheric Dispersal of Bioactive Streptomyces albidoflavus Strains Among Terrestrial and Marine Environments. Microb Ecol. 2016 Feb;71(2):375-86. doi: 10.1007/s00248-015-0654-z. Epub 2015 Jul 30. PMID: 26224165. 8: Li J, Xie Z, Wang M, Ai G, Chen Y. Identification and analysis of the paulomycin biosynthetic gene cluster and titer improvement of the paulomycins in Streptomyces paulus NRRL 8115. PLoS One. 2015 Mar 30;10(3):e0120542. doi: 10.1371/journal.pone.0120542. PMID: 25822496; PMCID: PMC4425429. 9: Li P, Li J, Guo Z, Tang W, Han J, Meng X, Hao T, Zhu Y, Zhang L, Chen Y. An efficient blue-white screening based gene inactivation system for Streptomyces. Appl Microbiol Biotechnol. 2015 Feb;99(4):1923-33. doi: 10.1007/s00253-014-6369-0. Epub 2015 Jan 21. PMID: 25666782. 10: Braña AF, Rodríguez M, Pahari P, Rohr J, García LA, Blanco G. Activation and silencing of secondary metabolites in Streptomyces albus and Streptomyces lividans after transformation with cosmids containing the thienamycin gene cluster from Streptomyces cattleya. Arch Microbiol. 2014 May;196(5):345-55. doi: 10.1007/s00203-014-0977-z. Epub 2014 Mar 15. PMID: 24633227. 11: Olano C, García I, González A, Rodriguez M, Rozas D, Rubio J, Sánchez- Hidalgo M, Braña AF, Méndez C, Salas JA. Activation and identification of five clusters for secondary metabolites in Streptomyces albus J1074. Microb Biotechnol. 2014 May;7(3):242-56. doi: 10.1111/1751-7915.12116. Epub 2014 Mar 4. PMID: 24593309; PMCID: PMC3992020. 12: Argoudelis AD, Baczynskyj L, Mizsak SA, Shilliday FB. O-demethylpaulomycins A and B, U-77,802 and U-77,803, paulomenols A and B, new metabolites produced by Streptomyces paulus. J Antibiot (Tokyo). 1988 Oct;41(10):1316-30. doi: 10.7164/antibiotics.41.1316. PMID: 3192491. 13: Argoudelis AD, Baczynskyj L, Mizsak SA, Shilliday FB, Wiley PF. Structural relationships between senfolomycins and paulomycins. J Antibiot (Tokyo). 1988 Sep;41(9):1212-22. doi: 10.7164/antibiotics.41.1212. PMID: 3141336. 14: Sanchez MS, Ford CW, Yancey RJ Jr. Evaluation of antibiotic effectiveness against Staphylococcus aureus surviving within the bovine mammary gland macrophage. J Antimicrob Chemother. 1988 Jun;21(6):773-86. doi: 10.1093/jac/21.6.773. PMID: 3410801. 15: Laborde AL, Cialdella JI, Shilliday FB, Marshall VP. Precursor directed biosynthesis of paulomycin C by methionine. J Antibiot (Tokyo). 1988 Feb;41(2):253-4. doi: 10.7164/antibiotics.41.253. PMID: 3356614. 16: Argoudelis AD, Baczynskyj L, Haak WJ, Knoll WM, Mizsak SA, Shilliday FB. New paulomycins produced by Streptomyces paulus. J Antibiot (Tokyo). 1988 Feb;41(2):157-69. doi: 10.7164/antibiotics.41.157. PMID: 3356604. 17: Majer J, Chater KF. Streptomyces albus G produces an antibiotic complex identical to paulomycins A and B. J Gen Microbiol. 1987 Sep;133(9):2503-7. doi: 10.1099/00221287-133-9-2503. PMID: 3448155. 18: Eliopoulos GM, Reiszner E, Moellering RC Jr. In vitro evaluation of the new paulomycin antibiotic paldimycin. Eur J Clin Microbiol. 1987 Jun;6(3):306-8. doi: 10.1007/BF02017620. PMID: 3622497. 19: Argoudelis AD, Baczynskyj L, Buege JA, Marshall VP, Mizsak SA, Wiley PF. Paulomycin-related antibiotics: paldimycins and antibiotics 273a2. Isolation and characterization. J Antibiot (Tokyo). 1987 Apr;40(4):408-18. doi: 10.7164/antibiotics.40.408. PMID: 3583912. 20: Argoudelis AD, Baczynskyj L, Mizsak SA, Shilliday FB, Spinelli PA, DeZwaan J. Paldimycins A and B and antibiotics 273a2 alpha and 273a2 beta. Synthesis and characterization. J Antibiot (Tokyo). 1987 Apr;40(4):419-36. doi: 10.7164/antibiotics.40.419. PMID: 3294773.