MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 464631 | Name: Lugdunin

Description:

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

Lugdunin is a thiazolidine-containing cyclic peptide antibiotic, suppressing growth of species of disease-causing bacteria in that part of the human microbiome.

Chemical Structure

Lugdunin
Lugdunin
CAS#1989698-37-4

Theoretical Analysis

MedKoo Cat#: 464631

Name: Lugdunin

CAS#: 1989698-37-4

Chemical Formula: C40H62N8O6S

Exact Mass: 782.4513

Molecular Weight: 783.05

Elemental Analysis: C, 61.36; H, 7.98; N, 14.31; O, 12.26; S, 4.09

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Lugdunin;
IUPAC/Chemical Name
(1R,4R,7S,10R,13S,16R,19S)-7-((1H-indol-3-yl)methyl)-10-isobutyl-4,13,16,19-tetraisopropyl-21-thia-3,6,9,12,15,18,23-heptaazabicyclo[18.2.1]tricosane-2,5,8,11,14,17-hexaone
InChi Key
QZNGYMKAHFFKCJ-ZBQZSICZSA-N
InChi Code
InChI=1S/C40H62N8O6S/c1-19(2)15-27-35(50)45-31(21(5)6)38(53)47-32(22(7)8)39(54)48-33(23(9)10)40-44-29(18-55-40)36(51)46-30(20(3)4)37(52)43-28(34(49)42-27)16-24-17-41-26-14-12-11-13-25(24)26/h11-14,17,19-23,27-33,40-41,44H,15-16,18H2,1-10H3,(H,42,49)(H,43,52)(H,45,50)(H,46,51)(H,47,53)(H,48,54)/t27-,28+,29+,30-,31+,32-,33+,40?/m1/s1
SMILES Code
O=C(N[C@H](C(C)C)C(N[C@@H](CC1=CNC2=C1C=CC=C2)C(N[C@H](CC(C)C)C(N[C@@H](C(C)C)C(N[C@@H]3C(C)C)=O)=O)=O)=O)[C@](N4)([H])CSC4[C@H](C(C)C)NC3=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

Preparing Stock Solutions

The following data is based on the product molecular weight 783.05 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: Saur JS, Wirtz SN, Schilling NA, Krismer B, Peschel A, Grond S. Distinct Lugdunins from a New Efficient Synthesis and Broad Exploitation of Its MRSA- Antimicrobial Structure. J Med Chem. 2021 Apr 8;64(7):4034-4058. doi: 10.1021/acs.jmedchem.0c02170. Epub 2021 Mar 29. PMID: 33779184. 2: Heilbronner S, Foster TJ. Staphylococcus lugdunensis: a Skin Commensal with Invasive Pathogenic Potential. Clin Microbiol Rev. 2020 Dec 23;34(2):e00205-20. doi: 10.1128/CMR.00205-20. PMID: 33361142; PMCID: PMC7950365. 3: Krauss S, Zipperer A, Wirtz S, Saur J, Konnerth MC, Heilbronner S, Torres Salazar BO, Grond S, Krismer B, Peschel A. Secretion of and Self-Resistance to the Novel Fibupeptide Antimicrobial Lugdunin by Distinct ABC Transporters in Staphylococcus lugdunensis. Antimicrob Agents Chemother. 2020 Dec 16;65(1):e01734-20. doi: 10.1128/AAC.01734-20. PMID: 33106269; PMCID: PMC7927808. 4: Bitschar K, Sauer B, Focken J, Dehmer H, Moos S, Konnerth M, Schilling NA, Grond S, Kalbacher H, Kurschus FC, Götz F, Krismer B, Peschel A, Schittek B. Lugdunin amplifies innate immune responses in the skin in synergy with host- and microbiota-derived factors. Nat Commun. 2019 Jun 21;10(1):2730. doi: 10.1038/s41467-019-10646-7. PMID: 31227691; PMCID: PMC6588697. 5: Blanco MJ. Building upon Nature's Framework: Overview of Key Strategies Toward Increasing Drug-Like Properties of Natural Product Cyclopeptides and Macrocycles. Methods Mol Biol. 2019;2001:203-233. doi: 10.1007/978-1-4939-9504-2_10. PMID: 31134573. 6: Schilling NA, Berscheid A, Schumacher J, Saur JS, Konnerth MC, Wirtz SN, Beltrán-Beleña JM, Zipperer A, Krismer B, Peschel A, Kalbacher H, Brötz- Oesterhelt H, Steinem C, Grond S. Synthetic Lugdunin Analogues Reveal Essential Structural Motifs for Antimicrobial Action and Proton Translocation Capability. Angew Chem Int Ed Engl. 2019 Jul 1;58(27):9234-9238. doi: 10.1002/anie.201901589. Epub 2019 May 27. PMID: 31059155; PMCID: PMC6618241. 7: Durand GA, Raoult D, Dubourg G. Antibiotic discovery: history, methods and perspectives. Int J Antimicrob Agents. 2019 Apr;53(4):371-382. doi: 10.1016/j.ijantimicag.2018.11.010. Epub 2018 Nov 23. PMID: 30472287. 8: Milshteyn A, Colosimo DA, Brady SF. Accessing Bioactive Natural Products from the Human Microbiome. Cell Host Microbe. 2018 Jun 13;23(6):725-736. doi: 10.1016/j.chom.2018.05.013. PMID: 29902438; PMCID: PMC7232905. 9: Zipperer A, Konnerth MC, Laux C, Berscheid A, Janek D, Weidenmaier C, Burian M, Schilling NA, Slavetinsky C, Marschal M, Willmann M, Kalbacher H, Schittek B, Brötz-Oesterhelt H, Grond S, Peschel A, Krismer B. Human commensals producing a novel antibiotic impair pathogen colonization. Nature. 2016 Jul 28;535(7613):511-6. doi: 10.1038/nature18634. Erratum in: Nature. 2016 Nov 10;539(7628):314. PMID: 27466123.