Laspartomycin C | CAS#unknown | Lipopeptide antibiotic

MedKoo Cat#: 465836 | Name: Laspartomycin C

Description:

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

Laspartomycin C is a lipopeptide antibiotic with activity against a range of Gram-positive bacteria including drug-resistant pathogens.

Chemical Structure

Laspartomycin C

CAS#unknown

Theoretical Analysis

MedKoo Cat#: 465836

Name: Laspartomycin C

CAS#: unknown

Chemical Formula: C57H90N12O19

Exact Mass: 1246.6445

Molecular Weight: 1247.41

Elemental Analysis: C, 54.88; H, 7.27; N, 13.47; O, 24.37

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

Laspartomycin C; Laspartomycin-C;

IUPAC/Chemical Name

2,2'-((6S,9S,15S,21S,33S,36aS)-6-((R)-sec-butyl)-33-((S)-3-carboxy-2-((E)-13-methyltetradec-2-enamido)propanamido)-9-((R)-1-hydroxyethyl)-5,8,11,14,17,20,23,26,32,36-decaoxotetratriacontahydro-1H,5H-pyrido[1,2-a]pyrrolo[1,2-y][1,4,7,10,13,16,19,22,25,28]decaazacyclohentriacontine-15,21-diyl)diacetic acid

InChi Key

JHAQMJWHVDTRJM-OIBPZYLOSA-N

InChi Code

InChI=1S/C57H90N12O19/c1-6-33(4)48-57(88)69-24-18-21-40(69)53(84)58-28-38(65-52(83)37(27-47(79)80)62-41(71)22-15-13-11-9-7-8-10-12-14-19-32(2)3)56(87)68-23-17-16-20-39(68)54(85)61-30-43(73)64-35(25-45(75)76)50(81)59-29-42(72)63-36(26-46(77)78)51(82)60-31-44(74)66-49(34(5)70)55(86)67-48/h15,22,32-40,48-49,70H,6-14,16-21,23-31H2,1-5H3,(H,58,84)(H,59,81)(H,60,82)(H,61,85)(H,62,71)(H,63,72)(H,64,73)(H,65,83)(H,66,74)(H,67,86)(H,75,76)(H,77,78)(H,79,80)/b22-15+/t33-,34-,35+,36+,37+,38+,39?,40+,48+,49+/m1/s1

SMILES Code

O=C(O)C[C@H](NC(/C=C/CCCCCCCCCC(C)C)=O)C(N[C@@H](CNC([C@]1([H])CCCN1C([C@H]([C@@H](CC)C)NC([C@H]([C@H](O)C)NC(CNC([C@H](CC(O)=O)NC(CNC([C@H](CC(O)=O)NC(CN2)=O)=O)=O)=O)=O)=O)=O)=O)C(N3CCCCC3C2=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

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 1,247.41 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: Diehl A, Wood TM, Gebhard S, Martin NI, Fritz G. The Cell Envelope Stress Response of Bacillus subtilis towards Laspartomycin C. Antibiotics (Basel). 2020 Oct 23;9(11):729. doi: 10.3390/antibiotics9110729. PMID: 33114184; PMCID: PMC7690785. 2: Kleijn LH, Oppedijk SF, 't Hart P, van Harten RM, Martin-Visscher LA, Kemmink J, Breukink E, Martin NI. Total Synthesis of Laspartomycin C and Characterization of Its Antibacterial Mechanism of Action. J Med Chem. 2016 Apr 14;59(7):3569-74. doi: 10.1021/acs.jmedchem.6b00219. Epub 2016 Mar 24. PMID: 26967152. 3: Kleijn LHJ, Vlieg HC, Wood TM, Sastre Toraño J, Janssen BJC, Martin NI. A High-Resolution Crystal Structure that Reveals Molecular Details of Target Recognition by the Calcium-Dependent Lipopeptide Antibiotic Laspartomycin C. Angew Chem Int Ed Engl. 2017 Dec 22;56(52):16546-16549. doi: 10.1002/anie.201709240. Epub 2017 Nov 30. PMID: 29108098; PMCID: PMC5767759. 4: Curran WV, Leese RA, Jarolmen H, Borders DB, Dugourd D, Chen Y, Cameron DR. Semisynthetic approaches to laspartomycin analogues. J Nat Prod. 2007 Mar;70(3):447-50. doi: 10.1021/np068062b. Epub 2007 Feb 27. PMID: 17323996. 5: Borders DB, Leese RA, Jarolmen H, Francis ND, Fantini AA, Falla T, Fiddes JC, Aumelas A. Laspartomycin, an acidic lipopeptide antibiotic with a unique peptide core. J Nat Prod. 2007 Mar;70(3):443-6. doi: 10.1021/np068056f. Epub 2007 Feb 22. PMID: 17315928. 6: Wang Y, Chen Y, Shen Q, Yin X. Molecular cloning and identification of the laspartomycin biosynthetic gene cluster from Streptomyces viridochromogenes. Gene. 2011 Sep 1;483(1-2):11-21. doi: 10.1016/j.gene.2011.05.005. Epub 2011 May 27. PMID: 21640802; PMCID: PMC3391544. 7: 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.