N-Formyl-Met-Leu-Phe
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MedKoo CAT#: 530953

CAS#: 59880-97-6

Description: N-Formyl-Met-Leu-Phe, also known as fMLF, is a potent neutrophil chemoattractant and the reference agonist for the G protein-coupled N-formylpeptide receptor (FPR).


Price and Availability

Size Price Shipping out time Quantity
10mg USD 250 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-31. Prices are subject to change without notice.

N-Formyl-Met-Leu-Phe, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

No image available

Theoretical Analysis

MedKoo Cat#: 530953
Name: N-Formyl-Met-Leu-Phe
CAS#: 59880-97-6
Chemical Formula: C21H31N3O5S
Exact Mass: 437.1984
Molecular Weight: 437.555
Elemental Analysis: C, 57.65; H, 7.14; N, 9.60; O, 18.28; S, 7.33


Synonym: Chemotactic peptide; N-Formyl-Met-Leu-Phe, FMLP; fMLF.

IUPAC/Chemical Name: N-Formylmethionyl-leucylphenylalanine

InChi Key: PRQROPMIIGLWRP-BZSNNMDCSA-N

InChi Code: InChI=1S/C21H31N3O5S/c1-14(2)11-17(23-19(26)16(22-13-25)9-10-30-3)20(27)24-18(21(28)29)12-15-7-5-4-6-8-15/h4-8,13-14,16-18H,9-12H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)(H,28,29)/t16-,17-,18-/m0/s1

SMILES Code: O=C(O)[C@H](CC1=CC=CC=C1)NC([C@H](CC(C)C)NC([C@H](CCSC)NC=O)=O)=O


Technical Data

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:
>2 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:
2934.99.9001


References

1: Hu Y, Cheng N, Wu H, Kang S, Ye RD, Cai J. Design, synthesis and characterization of fMLF-mimicking AApeptides. Chembiochem. 2014 Nov 3;15(16):2420-6. doi: 10.1002/cbic.201402396. Epub 2014 Sep 15. PubMed PMID: 25224835; PubMed Central PMCID: PMC4259043.

2: He HQ, Liao D, Wang ZG, Wang ZL, Zhou HC, Wang MW, Ye RD. Functional characterization of three mouse formyl peptide receptors. Mol Pharmacol. 2013 Feb;83(2):389-98. doi: 10.1124/mol.112.081315. Epub 2012 Nov 15. PubMed PMID: 23160941; PubMed Central PMCID: PMC4170117.

3: Zhang XG, Hui YN, Huang XF, Du HJ, Zhou J, Ma JX. Activation of formyl peptide receptor-1 enhances restitution of human retinal pigment epithelial cell monolayer under electric fields. Invest Ophthalmol Vis Sci. 2011 May 16;52(6):3160-5. doi: 10.1167/iovs.10-5156. PubMed PMID: 21228377.

4: Sogawa Y, Ohyama T, Maeda H, Hirahara K. Inhibition of neutrophil migration in mice by mouse formyl peptide receptors 1 and 2 dual agonist: indication of cross-desensitization in vivo. Immunology. 2011 Mar;132(3):441-50. doi: 10.1111/j.1365-2567.2010.03367.x. Epub 2010 Oct 29. PubMed PMID: 21039475; PubMed Central PMCID: PMC3044910.

5: Movitz C, Brive L, Hellstrand K, Rabiet MJ, Dahlgren C. The annexin I sequence gln(9)-ala(10)-trp(11)-phe(12) is a core structure for interaction with the formyl peptide receptor 1. J Biol Chem. 2010 May 7;285(19):14338-45. doi: 10.1074/jbc.M109.080465. Epub 2010 Mar 10. PubMed PMID: 20220135; PubMed Central PMCID: PMC2863206.

6: Southgate EL, He RL, Gao JL, Murphy PM, Nanamori M, Ye RD. Identification of formyl peptides from Listeria monocytogenes and Staphylococcus aureus as potent chemoattractants for mouse neutrophils. J Immunol. 2008 Jul 15;181(2):1429-37. PubMed PMID: 18606697; PubMed Central PMCID: PMC2705627.

7: Zhou C, Zhang S, Nanamori M, Zhang Y, Liu Q, Li N, Sun M, Tian J, Ye PP, Cheng N, Ye RD, Wang MW. Pharmacological characterization of a novel nonpeptide antagonist for formyl peptide receptor-like 1. Mol Pharmacol. 2007 Oct;72(4):976-83. Epub 2007 Jul 25. Erratum in: Mol Pharmacol. 2007 Nov;72(5):1391. PubMed PMID: 17652444.