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Description: Unnatural dipeptide building block with alkyne group for functionalizing peptidoglycan
Chemical Name: N-(4,4,5,5-Tetradehydro-D-norvalyl)-D-alanine trifluoroacetate
Purity: ≥95% (HPLC)
Literature (1)

Biological Activity for EDA-DA

EDA-DA is an unnatural dipeptide building block (an ethynyl-D-alanine and a D-alanine). It incorporates a biorthogonal alkyne group into peptidoglycan (PG) through MurF in the cytoplasmic pathway, which enables selective labeling via a click-chemistry reaction. EDA-DA allows labeling of PG in Gram-positive (B. subtilis), Gram-negative (E. coli and C. trachomatis), Mycobacterium (M. smegmatis) and moss plastids (P. patens) with azide modified fluorescent dyes such as Alexa Fluor 488.

Technical Data for EDA-DA

M. Wt 298.22
Formula C8H12N2O3.CF3CO2H
Storage Store at -20°C
Purity ≥95% (HPLC)
CAS Number 87156-01-2
Smiles C[C@H](C(O)=O)NC([C@@H](CC#C)N)=O.FC(F)(F)C(O)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for EDA-DA

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 29.82 100
water 29.82 100

Preparing Stock Solutions for EDA-DA

The following data is based on the product molecular weight 298.22. 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.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.35 mL 16.77 mL 33.53 mL
5 mM 0.67 mL 3.35 mL 6.71 mL
10 mM 0.34 mL 1.68 mL 3.35 mL
50 mM 0.07 mL 0.34 mL 0.67 mL

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References for EDA-DA

References are publications that support the biological activity of the product.

Cheung et al (1983) Chloralanyl and propargylglycyl dipeptides. Suicide substrate containing antibacterials. J.Med.Chem. 26 1733 PMID: 6417332

Liechti et al (2013) A new metabolic cell-wall labelling method reveals peptidoglycan in Chlamydia trachomatis. Nature 506 507 PMID: 24336210

Hirano et al (2016) Moss chloroplasts are surrounded by a peptidoglycan wall containing D-amino acids. Plant Cell 28 1521 PMID: 27325639

Kuru et al (2019) Mechanisms of incorporation for D-amino acid probes that target peptidoglycan biosynthesis. ACS Chem.Biol. 14 2745 PMID: 31743648

Banahene et al (2022) Chemical reporters for bacterial glycans: development and applications. Chem.Rev. 122 3336 PMID: 34905344

If you know of a relevant reference for EDA-DA, please let us know.

Keywords: EDA-DA, EDA-DA supplier, unnatural, dipeptide, ethynyl-D-alanine, alkyne, selective, labeling, peptidoglycan, Gram-positive, Gram-negative, Mycobacterium, bacteria, Fluorescent, Probes, for, Imaging, Bacteria, Unnatural, Amino, Acids, 7714, Tocris Bioscience

Citations for EDA-DA

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