Laterocidine | CAS# | Antibiotic

MedKoo Cat#: 130514 | Name: Laterocidine

Description:

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

Laterocidine is a macrocyclic lipodepsipeptide antibiotic, exhibiting potent antimicrobial activity toward Gram-negative bacteria and has a low risk of antibiotic resistance development. These bacteria include Pseudonomas aeruginosa and colistin-resistant E. coli.

Chemical Structure

Laterocidine

CAS#Laterocidine

Theoretical Analysis

MedKoo Cat#: 130514

Name: Laterocidine

CAS#: Laterocidine

Chemical Formula: C78H113N19O18

Exact Mass: 1603.8511

Molecular Weight: 1604.88

Elemental Analysis: C, 58.38; H, 7.10; N, 16.58; O, 17.94

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

CHEMBL4878048

IUPAC/Chemical Name

N-[(2R)-1-[[(2R)-1-[[(2R)-1-[[(2R)-5-amino-1-[[(2S)-5-amino-1-[[2-[[(2R)-5-amino-1-[[(2S)-1-[[(9S,12S,15S,16R)-9-(2-amino-2-oxoethyl)-12-[(2S)-butan-2-yl]-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-15-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]-7-methyloctanamide

InChi Key

MIUUXMLKAKRFMK-PCBFYWCHSA-N

InChi Code

InChI=1S/C78H113N19O18/c1-6-44(4)67-77(113)95-60(36-62(82)100)70(106)86-39-64(102)85-41-66(104)115-45(5)68(78(114)96-67)97-75(111)59(35-48-38-84-53-21-13-11-19-51(48)53)93-71(107)55(23-15-31-80)88-65(103)40-87-69(105)54(22-14-30-79)90-72(108)56(24-16-32-81)91-74(110)58(34-47-37-83-52-20-12-10-18-50(47)52)94-73(109)57(33-46-26-28-49(99)29-27-46)92-76(112)61(42-98)89-63(101)25-9-7-8-17-43(2)3/h10-13,18-21,26-29,37-38,43-45,54-61,67-68,83-84,98-99H,6-9,14-17,22-25,30-36,39-42,79-81H2,1-5H3,(H2,82,100)(H,85,102)(H,86,106)(H,87,105)(H,88,103)(H,89,101)(H,90,108)(H,91,110)(H,92,112)(H,93,107)(H,94,109)(H,95,113)(H,96,114)(H,97,111)/t44-,45+,54-,55+,56+,57+,58+,59-,60-,61+,67-,68-/m0/s1

SMILES Code

CC(C)CCCCCC(N[C@H](CO)C(N[C@H](CC1=CC=C(O)C=C1)C(N[C@H](CC2=CNC3=C2C=CC=C3)C(N[C@H](CCCN)C(N[C@@H](CCCN)C(NCC(N[C@H](CCCN)C(N[C@@H](CC4=CNC5=C4C=CC=C5)C(N[C@@H]6C(N[C@@H]([C@H](CC)C)C(N[C@@H](CC(N)=O)C(NCC(NCC(O[C@@H]6C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O

Appearance

To be determined

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 1,604.88 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. Ballantine RD, Al Ayed K, Bann SJ, Hoekstra M, Martin NI, Cochrane SA. Linearization of the Brevicidine and Laterocidine Lipopeptides Yields Analogues That Retain Full Antibacterial Activity. J Med Chem. 2023 Apr 27;66(8):6002-6009. doi: 10.1021/acs.jmedchem.3c00308. Epub 2023 Apr 18. PMID: 37071814; PMCID: PMC10150354. 2. Ballantine RD, Al Ayed K, Bann SJ, Hoekstra M, Martin NI, Cochrane SA. Synthesis and structure-activity relationship studies of N-terminal analogues of the lipopeptide antibiotics brevicidine and laterocidine. RSC Med Chem. 2022 Oct 27;13(12):1640-1643. doi: 10.1039/d2md00281g. PMID: 36545437; PMCID: PMC9749936. 3. Hermant Y, Palpal-Latoc D, Kovalenko N, Cameron AJ, Brimble MA, Harris PWR. The Total Chemical Synthesis and Biological Evaluation of the Cationic Antimicrobial Peptides, Laterocidine and Brevicidine. J Nat Prod. 2021 Aug 27;84(8):2165-2174. doi: 10.1021/acs.jnatprod.1c00222. Epub 2021 Aug 2. PMID: 34338512. 4. Wang Z, Koirala B, Hernandez Y, Brady SF. Discovery of Paenibacillaceae Family Gram-Negative-Active Cationic Lipopeptide Antibiotics Using Evolution-Guided Chemical Synthesis. Org Lett. 2022 Jul 15;24(27):4943-4948. doi: 10.1021/acs.orglett.2c01879. Epub 2022 Jul 1. PMID: 35776528; PMCID: PMC10234496. 5. Al Ayed K, Ballantine RD, Hoekstra M, Bann SJ, Wesseling CMJ, Bakker AT, Zhong Z, Li YX, Brüchle NC, van der Stelt M, Cochrane SA, Martin NI. Synthetic studies with the brevicidine and laterocidine lipopeptide antibiotics including analogues with enhanced properties and in vivo efficacy. Chem Sci. 2022 Feb 23;13(12):3563-3570. doi: 10.1039/d2sc00143h. PMID: 35432860; PMCID: PMC8943889. 6. Li YX, Zhong Z, Zhang WP, Qian PY. Discovery of cationic nonribosomal peptides as Gram-negative antibiotics through global genome mining. Nat Commun. 2018 Aug 16;9(1):3273. doi: 10.1038/s41467-018-05781-6. PMID: 30115920; PMCID: PMC6095874. 7. Al Ayed K, Zamarbide Losada D, Machushynets NV, Terlouw B, Elsayed SS, Schill J, Trebosc V, Pieren M, Medema MH, van Wezel GP, Martin NI. Total Synthesis and Structure Assignment of the Relacidine Lipopeptide Antibiotics and Preparation of Analogues with Enhanced Stability. ACS Infect Dis. 2023 Apr 14;9(4):739-748. doi: 10.1021/acsinfecdis.3c00043. Epub 2023 Mar 31. PMID: 37000899; PMCID: PMC10111413.