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MedKoo Cat#: 592473 | Name: Picromycin
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Description:

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

Picromycin is a 14-membered macrolide antibiotic and inhibitor of Prolyl endopeptidase (PREP). Pikromycin shows activity against gram-positive bacteria including mycobacteria.

Chemical Structure

Picromycin
Picromycin
CAS#19721-56-3

Theoretical Analysis

MedKoo Cat#: 592473

Name: Picromycin

CAS#: 19721-56-3

Chemical Formula: C28H47NO8

Exact Mass: 525.3302

Molecular Weight: 525.68

Elemental Analysis: C, 63.98; H, 9.01; N, 2.66; O, 24.35

Price and Availability

Size Price Availability Quantity
2.5mg USD 695.00 2 Weeks
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Related CAS #
No Data
Synonym
Picromycin; Pikromycin, Antibiotic B 62169A; Albomycetin; Amaromycin;
IUPAC/Chemical Name
(3R,5R,6S,7S,9R,13S,14R,E)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-13-hydroxy-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione
InChi Key
UZQBOFAUUTZOQE-VSLWXVDYSA-N
InChi Code
InChI=1S/C28H47NO8/c1-10-22-28(7,34)12-11-21(30)15(2)13-16(3)25(18(5)23(31)19(6)26(33)36-22)37-27-24(32)20(29(8)9)14-17(4)35-27/h11-12,15-20,22,24-25,27,32,34H,10,13-14H2,1-9H3/b12-11+/t15-,16+,17-,18+,19-,20+,22-,24-,25+,27+,28+/m1/s1
SMILES Code
CC[C@H]1OC([C@@H](C([C@@H]([C@H]([C@H](C[C@H](C(/C=C/[C@@]1(O)C)=O)C)C)O[C@@H]2O[C@@H](C[C@H](N(C)C)[C@H]2O)C)C)=O)C)=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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pikromycin is a macrolide antibiotic that has been found in S. venezuelae and active against E. coli, S. aureus and B. subtilis.
In vitro activity:
TBD
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 525.68 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
Formulation protocol:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Almutairi MM, Svetlov MS, Hansen DA, Khabibullina NF, Klepacki D, Kang HY, Sherman DH, Vázquez-Laslop N, Polikanov YS, Mankin AS. Co-produced natural ketolides methymycin and pikromycin inhibit bacterial growth by preventing synthesis of a limited number of proteins. Nucleic Acids Res. 2017 Sep 19;45(16):9573-9582. doi: 10.1093/nar/gkx673. PubMed PMID: 28934499; PubMed Central PMCID: PMC5766166. 2: Goldberg VE, Polyakova TY, Popova NO, Vysotskaya VV, Simolina EI, Belevich YV, Tuzikova TP, Goldberg AV, Zhdanov VV, Miroshnichenko LA, Udut EV, Simanina EV, Dygai AM, Zyuz'kov GN. Assessment of Erythroid and Granulocytic Hematopoietic Lineages in Patients with Non-Small-Cell Lung Carcinoma. Bull Exp Biol Med. 2017 Aug;163(4):469-474. doi: 10.1007/s10517-017-3830-y. Epub 2017 Aug 29. PubMed PMID: 28853075. 3: Hansen DA, Koch AA, Sherman DH. Identification of a Thioesterase Bottleneck in the Pikromycin Pathway through Full-Module Processing of Unnatural Pentaketides. J Am Chem Soc. 2017 Sep 27;139(38):13450-13455. doi: 10.1021/jacs.7b06432. Epub 2017 Sep 19. PubMed PMID: 28836772; PubMed Central PMCID: PMC5617803. 4: Koch AA, Hansen DA, Shende VV, Furan LR, Houk KN, Jiménez-Osés G, Sherman DH. A Single Active Site Mutation in the Pikromycin Thioesterase Generates a More Effective Macrocyclization Catalyst. J Am Chem Soc. 2017 Sep 27;139(38):13456-13465. doi: 10.1021/jacs.7b06436. Epub 2017 Sep 19. PubMed PMID: 28836768; PubMed Central PMCID: PMC5617804. 5: Pyeon HR, Nah HJ, Kang SH, Choi SS, Kim ES. Heterologous expression of pikromycin biosynthetic gene cluster using Streptomyces artificial chromosome system. Microb Cell Fact. 2017 May 31;16(1):96. doi: 10.1186/s12934-017-0708-7. PubMed PMID: 28569150; PubMed Central PMCID: PMC5452415. 6: Han S, Pham TV, Kim JH, Lim YR, Park HG, Jeong D, Yun CH, Chun YJ, Kang LW, Kim D. Structural insights into the binding of lauric acid to CYP107L2 from Streptomyces avermitilis. Biochem Biophys Res Commun. 2017 Jan 22;482(4):902-908. doi: 10.1016/j.bbrc.2016.11.131. Epub 2016 Nov 25. PubMed PMID: 27890614. 7: Tripathi A, Choi SS, Sherman DH, Kim ES. Thioesterase domain swapping of a linear polyketide tautomycetin with a macrocyclic polyketide pikromycin in Streptomyces sp. CK4412. J Ind Microbiol Biotechnol. 2016 Aug;43(8):1189-93. doi: 10.1007/s10295-016-1790-2. Epub 2016 Jun 9. PubMed PMID: 27277081; PubMed Central PMCID: PMC4939285. 8: Chemler JA, Tripathi A, Hansen DA, O'Neil-Johnson M, Williams RB, Starks C, Park SR, Sherman DH. Evolution of Efficient Modular Polyketide Synthases by Homologous Recombination. J Am Chem Soc. 2015 Aug 26;137(33):10603-9. doi: 10.1021/jacs.5b04842. Epub 2015 Aug 13. PubMed PMID: 26230368; PubMed Central PMCID: PMC4666801. 9: Li Y, Dodge GJ, Fiers WD, Fecik RA, Smith JL, Aldrich CC. Functional Characterization of a Dehydratase Domain from the Pikromycin Polyketide Synthase. J Am Chem Soc. 2015 Jun 10;137(22):7003-6. doi: 10.1021/jacs.5b02325. Epub 2015 Jun 2. PubMed PMID: 26027428; PubMed Central PMCID: PMC4624270. 10: Hansen DA, Koch AA, Sherman DH. Substrate controlled divergence in polyketide synthase catalysis. J Am Chem Soc. 2015 Mar 25;137(11):3735-8. doi: 10.1021/ja511743n. Epub 2015 Mar 12. PubMed PMID: 25730816; PubMed Central PMCID: PMC4379966. 11: Yi JS, Kim MS, Kim SJ, Kim BG. Effects of Sucrose, Phosphate, and Calcium Carbonate on the Production of Pikromycin from Streptomyces venezuelae. J Microbiol Biotechnol. 2015 Apr;25(4):496-502. PubMed PMID: 25341465. 12: Garg A, Xie X, Keatinge-Clay A, Khosla C, Cane DE. Elucidation of the cryptic epimerase activity of redox-inactive ketoreductase domains from modular polyketide synthases by tandem equilibrium isotope exchange. J Am Chem Soc. 2014 Jul 23;136(29):10190-3. doi: 10.1021/ja5056998. Epub 2014 Jul 10. PubMed PMID: 25004372; PubMed Central PMCID: PMC4111212. 13: Whicher JR, Dutta S, Hansen DA, Hale WA, Chemler JA, Dosey AM, Narayan AR, Håkansson K, Sherman DH, Smith JL, Skiniotis G. Structural rearrangements of a polyketide synthase module during its catalytic cycle. Nature. 2014 Jun 26;510(7506):560-4. doi: 10.1038/nature13409. Epub 2014 Jun 18. PubMed PMID: 24965656; PubMed Central PMCID: PMC4074775. 14: Dutta S, Whicher JR, Hansen DA, Hale WA, Chemler JA, Congdon GR, Narayan AR, Håkansson K, Sherman DH, Smith JL, Skiniotis G. Structure of a modular polyketide synthase. Nature. 2014 Jun 26;510(7506):512-7. doi: 10.1038/nature13423. Epub 2014 Jun 18. PubMed PMID: 24965652; PubMed Central PMCID: PMC4278352. 15: Hansen DA, Rath CM, Eisman EB, Narayan AR, Kittendorf JD, Mortison JD, Yoon YJ, Sherman DH. Biocatalytic synthesis of pikromycin, methymycin, neomethymycin, novamethymycin, and ketomethymycin. J Am Chem Soc. 2013 Jul 31;135(30):11232-8. doi: 10.1021/ja404134f. Epub 2013 Jul 18. PubMed PMID: 23866020; PubMed Central PMCID: PMC3771335. 16: Oh HS, Kang HY. Total synthesis of pikromycin. J Org Chem. 2012 Jan 20;77(2):1125-30. doi: 10.1021/jo201158q. Epub 2011 Dec 30. PubMed PMID: 22168449. 17: Bonnett SA, Rath CM, Shareef AR, Joels JR, Chemler JA, Håkansson K, Reynolds K, Sherman DH. Acyl-CoA subunit selectivity in the pikromycin polyketide synthase PikAIV: steady-state kinetics and active-site occupancy analysis by FTICR-MS. Chem Biol. 2011 Sep 23;18(9):1075-81. doi: 10.1016/j.chembiol.2011.07.016. PubMed PMID: 21944746; PubMed Central PMCID: PMC3184853. 18: Han AR, Park SR, Park JW, Lee EY, Kim DM, Kim BG, Yoon YJ. Biosynthesis of glycosylated derivatives of tylosin in Streptomyces venezuelae. J Microbiol Biotechnol. 2011 Jun;21(6):613-6. PubMed PMID: 21715968. 19: Borisova SA, Liu HW. Characterization of glycosyltransferase DesVII and its auxiliary partner protein DesVIII in the methymycin/picromycin biosynthetic pathway. Biochemistry. 2010 Sep 21;49(37):8071-84. doi: 10.1021/bi1007657. PubMed PMID: 20695498; PubMed Central PMCID: PMC2939310. 20: Mortison JD, Kittendorf JD, Sherman DH. Synthesis and biochemical analysis of complex chain-elongation intermediates for interrogation of molecular specificity in the erythromycin and pikromycin polyketide synthases. J Am Chem Soc. 2009 Nov 4;131(43):15784-93. doi: 10.1021/ja9060596. PubMed PMID: 19810731; PubMed Central PMCID: PMC2796446.

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