Sansanmycin | CAS# | Uridyl peptide antibiotic

MedKoo Cat#: 208041 | Name: Sansanmycin

Description:

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

Sansanmycin is a uridyl peptide antibiotic, exhibiting antibacterial activity against Mycobacterium tuberculosis H(37)Ra and Pseudomonas aeruginosa with MIC values of 10 and 12.5 mug/ml, respectively.

Chemical Structure

Sansanmycin

CAS#N/A

Theoretical Analysis

MedKoo Cat#: 208041

Name: Sansanmycin

CAS#: N/A

Chemical Formula: C40H49N9O11S

Exact Mass: 863.3272

Molecular Weight: 863.94

Elemental Analysis: C, 55.61; H, 5.72; N, 14.59; O, 20.37; S, 3.71

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

Sansanmycin

IUPAC/Chemical Name

(((2S)-1-(((3S)-3-((S)-2-amino-3-(3-hydroxyphenyl)-N-methylpropanamido)-1-(((Z)-((4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxydihydrofuran-2(3H)-ylidene)methyl)amino)-1-oxobutan-2-yl)amino)-4-(methylthio)-1-oxobutan-2-yl)carbamoyl)tryptophan

InChi Key

JTNZPPUDLUHMKK-IXRYSDHVSA-N

InChi Code

InChI=1S/C40H49N9O11S/c1-21(48(2)36(55)27(41)16-22-7-6-8-24(50)15-22)33(35(54)43-20-25-18-31(51)37(60-25)49-13-11-32(52)46-40(49)59)47-34(53)29(12-14-61-3)44-39(58)45-30(38(56)57)17-23-19-42-28-10-5-4-9-26(23)28/h4-11,13,15,19-21,27,29-31,33,37,42,50-51H,12,14,16-18,41H2,1-3H3,(H,43,54)(H,47,53)(H,56,57)(H2,44,45,58)(H,46,52,59)/b25-20-/t21-,27-,29-,30?,31+,33?,37+/m0/s1

SMILES Code

OC(C(NC(N[C@@H](CCSC)C(NC(C(N/C=C1C[C@@H](O)[C@H](N2C=CC(NC2=O)=O)O/1)=O)[C@@H](N(C([C@H](CC3=CC(O)=CC=C3)N)=O)C)C)=O)=O)CC4=CNC5=CC=CC=C54)=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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 863.94 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.

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: Tran W, Kusay AS, Hawkins PME, Cheung CY, Nagalingam G, Pujari V, Ford DJ, Stoye A, Ochoa JL, Audette RE, Hortle E, Oehlers SH, Charman SA, Linington RG, Rubin EJ, Dowson CG, Roper DI, Crick DC, Balle T, Cook GM, Britton WJ, Payne RJ. Synthetic Sansanmycin Analogues as Potent Mycobacterium tuberculosis Translocase I Inhibitors. J Med Chem. 2021 Dec 9;64(23):17326-17345. doi: 10.1021/acs.jmedchem.1c01407. Epub 2021 Nov 30. PMID: 34845906. 2: Liu N, Guan H, Niu G, Jiang L, Li Y, Zhang J, Li J, Tan H. Molecular mechanism of mureidomycin biosynthesis activated by introduction of an exogenous regulatory gene ssaA into Streptomyces roseosporus. Sci China Life Sci. 2021 Nov;64(11):1949-1963. doi: 10.1007/s11427-020-1892-3. Epub 2021 Feb 9. PMID: 33580428; PMCID: PMC7880210. 3: Niro G, Weck SC, Ducho C. Merging Natural Products: Muraymycin-Sansanmycin Hybrid Structures as Novel Scaffolds for Potential Antibacterial Agents. Chemistry. 2020 Dec 15;26(70):16875-16887. doi: 10.1002/chem.202003387. Epub 2020 Nov 16. PMID: 32897546; PMCID: PMC7756498. 4: Bugg TDH, Kerr RV. Mechanism of action of nucleoside antibacterial natural product antibiotics. J Antibiot (Tokyo). 2019 Dec;72(12):865-876. doi: 10.1038/s41429-019-0227-3. Epub 2019 Aug 30. PMID: 31471595. 5: Shi Y, Wang X, He N, Xie Y, Hong B. Rescrutiny of the sansanmycin biosynthetic gene cluster leads to the discovery of a novel sansanmycin analogue with more potency against Mycobacterium tuberculosis. J Antibiot (Tokyo). 2019 Oct;72(10):769-774. doi: 10.1038/s41429-019-0210-z. Epub 2019 Jul 24. PMID: 31341273. 6: Jiang ZB, Ren WC, Shi YY, Li XX, Lei X, Fan JH, Zhang C, Gu RJ, Wang LF, Xie YY, Hong B. Structure-based manual screening and automatic networking for systematically exploring sansanmycin analogues using high performance liquid chromatography tandem mass spectroscopy. J Pharm Biomed Anal. 2018 Sep 5;158:94-105. doi: 10.1016/j.jpba.2018.05.024. Epub 2018 May 18. PMID: 29885606. 7: Wang SS, Zhang NN, He N, Guo WQ, Lei X, Cai Q, Hong B, Xie YY. Exploiting Substrate Diversity of NRPS Led to the Generation of New Sansanmycin Analogs. Nat Prod Commun. 2017 May;12(5):781-783. PMID: 30496665. 8: Tran AT, Watson EE, Pujari V, Conroy T, Dowman LJ, Giltrap AM, Pang A, Wong WR, Linington RG, Mahapatra S, Saunders J, Charman SA, West NP, Bugg TD, Tod J, Dowson CG, Roper DI, Crick DC, Britton WJ, Payne RJ. Sansanmycin natural product analogues as potent and selective anti-mycobacterials that inhibit lipid I biosynthesis. Nat Commun. 2017 Mar 1;8:14414. doi: 10.1038/ncomms14414. PMID: 28248311; PMCID: PMC5337940. 9: Zhang N, Liu L, Shan G, Cai Q, Lei X, Hong B, Wu L, Xie Y, Chen R. Precursor- directed biosynthesis of new sansanmycin analogs bearing para-substituted- phenylalanines with high yields. J Antibiot (Tokyo). 2016 Oct;69(10):765-768. doi: 10.1038/ja.2016.2. Epub 2016 Feb 24. PMID: 26905760. 10: Shi Y, Jiang Z, Lei X, Zhang N, Cai Q, Li Q, Wang L, Si S, Xie Y, Hong B. Improving the N-terminal diversity of sansanmycin through mutasynthesis. Microb Cell Fact. 2016 May 6;15:77. doi: 10.1186/s12934-016-0471-1. PMID: 27154005; PMCID: PMC4858918. 11: Jiang L, Wang L, Zhang J, Liu H, Hong B, Tan H, Niu G. Identification of novel mureidomycin analogues via rational activation of a cryptic gene cluster in Streptomyces roseosporus NRRL 15998. Sci Rep. 2015 Sep 15;5:14111. doi: 10.1038/srep14111. PMID: 26370924; PMCID: PMC4572928. 12: Xie Y, Cai Q, Ren H, Wang L, Xu H, Hong B, Wu L, Chen R. NRPS substrate promiscuity leads to more potent antitubercular sansanmycin analogues. J Nat Prod. 2014 Jul 25;77(7):1744-8. doi: 10.1021/np5001494. Epub 2014 Jun 25. PMID: 24964393. 13: Li Q, Wang L, Xie Y, Wang S, Chen R, Hong B. SsaA, a member of a novel class of transcriptional regulators, controls sansanmycin production in Streptomyces sp. strain SS through a feedback mechanism. J Bacteriol. 2013 May;195(10):2232-43. doi: 10.1128/JB.00054-13. Epub 2013 Mar 8. PMID: 23475969; PMCID: PMC3650532. 14: Wang L, Xie Y, Li Q, He N, Yao E, Xu H, Yu Y, Chen R, Hong B. Draft genome sequence of Streptomyces sp. strain SS, which produces a series of uridyl peptide antibiotic sansanmycins. J Bacteriol. 2012 Dec;194(24):6988-9. doi: 10.1128/JB.01916-12. PMID: 23209237; PMCID: PMC3510599. 15: Li YB, Xie YY, Du NN, Lu Y, Xu HZ, Wang B, Yu Y, Liu YX, Song DQ, Chen RX. Synthesis and in vitro antitubercular evaluation of novel sansanmycin derivatives. Bioorg Med Chem Lett. 2011 Nov 15;21(22):6804-7. doi: 10.1016/j.bmcl.2011.09.031. Epub 2011 Sep 16. PMID: 21982497. 16: Xie Y, Xu H, Sun C, Yu Y, Chen R. Two novel nucleosidyl-peptide antibiotics: Sansanmycin F and G produced by Streptomyces sp SS. J Antibiot (Tokyo). 2010 Mar;63(3):143-6. doi: 10.1038/ja.2010.6. Epub 2010 Feb 5. PMID: 20139866. 17: Li Y, Xie YY, Chen RX, Xu HZ, Zhang GJ, Li JZ, Li XM. Effects of combined treatment with sansanmycin and macrolides on Pseudomonas aeruginosa and formation of biofilm. Biomed Environ Sci. 2009 Apr;22(2):170-7. doi: 10.1016/S0895-3988(09)60042-8. PMID: 19618697. 18: Xie Y, Xu H, Si S, Sun C, Chen R. Sansanmycins B and C, new components of sansanmycins. J Antibiot (Tokyo). 2008 Apr;61(4):237-40. doi: 10.1038/ja.2008.34. PMID: 18503203. 19: Xie Y, Chen R, Si S, Sun C, Xu H. A new nucleosidyl-peptide antibiotic, sansanmycin. J Antibiot (Tokyo). 2007 Feb;60(2):158-61. doi: 10.1038/ja.2007.16. PMID: 17420567.