MedKoo Cat#: 599259 | Name: Lotilibcin

Description:

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

Lotilibcin is an antibiotic isolated from Staphylococcus aureus.

Chemical Structure

Lotilibcin
Lotilibcin
CAS#169148-84-9 (free base)

Theoretical Analysis

MedKoo Cat#: 599259

Name: Lotilibcin

CAS#: 169148-84-9 (free base)

Chemical Formula: C73H113N17O21

Exact Mass: 1563.8297

Molecular Weight: 1564.80

Elemental Analysis: C, 56.03; H, 7.28; N, 15.22; O, 21.47

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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Synonym
Lotilibcin; WAP-8294A2; WAP8294A2; WAP 8294A2
IUPAC/Chemical Name
(2S,5R,8R,11R,14S)-8-((1H-indol-3-yl)methyl)-14-((2R,5S,8R,14S,17R,20S)-17-((R)-2-amino-1-hydroxy-2-oxoethyl)-2-(3-aminopropyl)-8-benzyl-14,20-bis(hydroxymethyl)-5-isobutyl-9,28-dimethyl-4,7,10,13,16,19,22-heptaoxo-3,6,9,12,15,18,21-heptaazanonacosanamido)-11-(2-amino-2-oxoethyl)-5-(3-aminopropyl)-2-isopropyl-3-methyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazaheptadecanedioic acid
InChi Key
RLKMANLLJNAYAC-DONPJIOESA-N
InChi Code
InChI=1S/C73H113N17O21/c1-39(2)19-11-9-14-26-56(94)80-53(38-92)69(106)88-59(61(98)62(77)99)71(108)87-52(37-91)63(100)79-36-57(95)89(7)54(32-42-20-12-10-13-21-42)70(107)86-49(31-40(3)4)66(103)81-46(24-17-29-74)64(101)82-47(27-28-58(96)97)65(102)85-51(34-55(76)93)68(105)84-50(33-43-35-78-45-23-16-15-22-44(43)45)67(104)83-48(25-18-30-75)72(109)90(8)60(41(5)6)73(110)111/h10,12-13,15-16,20-23,35,39-41,46-54,59-61,78,91-92,98H,9,11,14,17-19,24-34,36-38,74-75H2,1-8H3,(H2,76,93)(H2,77,99)(H,79,100)(H,80,94)(H,81,103)(H,82,101)(H,83,104)(H,84,105)(H,85,102)(H,86,107)(H,87,108)(H,88,106)(H,96,97)(H,110,111)/t46-,47+,48-,49+,50-,51-,52+,53+,54-,59-,60+,61-/m1/s1
SMILES Code
O=C(O)CC[C@H](NC([C@@H](CCCN)NC([C@H](CC(C)C)NC([C@@H](CC1=CC=CC=C1)N(C)C(CNC([C@H](CO)NC([C@@H]([C@@H](O)C(N)=O)NC([C@H](CO)NC(CCCCCC(C)C)=O)=O)=O)=O)=O)=O)=O)=O)C(N[C@H](CC(N)=O)C(N[C@H](CC2=CNC3=C2C=CC=C3)C(N[C@H](CCCN)C(N(C)[C@@H](C(C)C)C(O)=O)=O)=O)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,564.80 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: Xu G, Zhao Y, Du L, Qian G, Liu F. Hfq regulates antibacterial antibiotic biosynthesis and extracellular lytic-enzyme production in Lysobacter enzymogenes OH11. Microb Biotechnol. 2015 May;8(3):499-509. doi: 10.1111/1751-7915.12246. Epub 2015 Feb 13. PubMed PMID: 25683974; PubMed Central PMCID: PMC4408182. 2: Zhang J, Du L, Liu F, Xu F, Hu B, Venturi V, Qian G. Involvement of both PKS and NRPS in antibacterial activity in Lysobacter enzymogenes OH11. FEMS Microbiol Lett. 2014 Jun;355(2):170-6. doi: 10.1111/1574-6968.12457. Epub 2014 Jun 3. PubMed PMID: 24801439; PubMed Central PMCID: PMC4106713. 3: Wang Y, Qian G, Liu F, Li YZ, Shen Y, Du L. Facile method for site-specific gene integration in Lysobacter enzymogenes for yield improvement of the anti-MRSA antibiotics WAP-8294A and the antifungal antibiotic HSAF. ACS Synth Biol. 2013 Nov 15;2(11):670-8. doi: 10.1021/sb4000806. Epub 2013 Aug 27. PubMed PMID: 23937053; PubMed Central PMCID: PMC3830728. 4: Kato A, Hirata H, Ohashi Y, Fujii K, Mori K, Harada K. A new anti-MRSA antibiotic complex, WAP-8294A II. Structure characterization of minor components by ESI LCMS and MS/MS. J Antibiot (Tokyo). 2011 May;64(5):373-9. doi: 10.1038/ja.2011.9. Epub 2011 Feb 16. PubMed PMID: 21326252. 5: Zhang W, Li Y, Qian G, Wang Y, Chen H, Li YZ, Liu F, Shen Y, Du L. Identification and characterization of the anti-methicillin-resistant Staphylococcus aureus WAP-8294A2 biosynthetic gene cluster from Lysobacter enzymogenes OH11. Antimicrob Agents Chemother. 2011 Dec;55(12):5581-9. doi: 10.1128/AAC.05370-11. Epub 2011 Sep 19. PubMed PMID: 21930890; PubMed Central PMCID: PMC3232812. 6: Kato A, Nakaya S, Kokubo N, Aiba Y, Ohashi Y, Hirata H, Fujii K, Harada K. A new anti-MRSA antibiotic complex, WAP-8294A. I. Taxonomy, isolation and biological activities. J Antibiot (Tokyo). 1998 Oct;51(10):929-35. PubMed PMID: 9917006. 7: Harad KI, Suzuki M, Kato A, Fujii K, Oka H, Ito Y. Separation of WAP-8294A components, a novel anti-methicillin-resistant staphylococcus aureus antibiotic, using high-speed counter-current chromatography. J Chromatogr A. 2001 Oct 12;932(1-2):75-81. PubMed PMID: 11695870. 8: Itoh H, Tokumoto K, Kaji T, Paudel A, Panthee S, Hamamoto H, Sekimizu K, Inoue M. Total Synthesis and Biological Mode of Action of WAP-8294A2: A Menaquinone-Targeting Antibiotic. J Org Chem. 2018 Jul 6;83(13):6924-6935. doi: 10.1021/acs.joc.7b02318. Epub 2017 Nov 7. PubMed PMID: 29019678. 9: Yu L, Su W, Fey PD, Liu F, Du L. Yield Improvement of the Anti-MRSA Antibiotics WAP-8294A by CRISPR/dCas9 Combined with Refactoring Self-Protection Genes in Lysobacter enzymogenes OH11. ACS Synth Biol. 2018 Jan 19;7(1):258-266. doi: 10.1021/acssynbio.7b00293. Epub 2017 Nov 20. PubMed PMID: 29125739; PubMed Central PMCID: PMC5775038.