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Description: Blue fluorescent D-amino acid for labeling peptidoglycans in live bacteria
Chemical Name: 3-[[(7-Hydroxy-2-oxo-2H-1-benzopyran-3-yl)carbonyl]amino]-D-alanine hydrocholoride
Purity: ≥98% (HPLC)
Biological Activity for HADA
HADA is a fluorescent D-amino acid. Suitable for labeling peptidoglycans in live bacteria. Results in strong peripheral and septal labeling of diverse bacterial cell populations without affecting growth rates. Displays mitochondrial outer membrane permeability. Excitation/emission λ ~405/450 nm.
Scientific Data
Investigating mycobacteria cell wall formation using FDAA HADA. Investigating mycobacteria cell wall formation using fluorescent D-amino acid HADA. Image showing FDAA HADA incorporation in log-phase growth of WT, delta L,D-transpeptidases (LDT) and delta L,D-transpeptidases (LDT) comp cells. Scale = 5 μm. Baranowski et al show FDAAs are incorporated asymmetrically by L,D-transpeptidases. For more information on this work and to request full protocols read Baranowski et al (2018) Maturing Mycobacterium smegmatis peptidoglycan requires non-canonical crosslinks to maintain shape. Elife 16 e37516 PMID: 30324906
Using FDAAs HADA and RADA to study peptidoglycan enzyme and substrate distribution, and the role of polar cell growth and peptidoglycan segregation over time. Image shows peptidoglycan segregation over time. Left to right - 2 mins HADA pulse (cyan), 45 min outgrowth, followed by 2 min RADA (Catalog # 6649) chase (magenta) in WT Msm cells. New cell wall (magenta), oldest cell wall (cyan). Scale = 5 μm. For more information on this work and to request full protocols please read García-Heredia et al (2018) Peptidoglycan precursor synthesis along the sidewall of pole-growing mycobacteria. Elife 10 e37243 PMID: 30198841
Optical Data for HADA
| Emission Color | Blue |
|---|---|
| λabs | 405 nm |
| λem | 450 nm |
| Extinction Coefficient (ε) | 36,700 M-1cm-1 |
| Application | Fluorescence Microscopy |
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Use our spectra viewer to interactively plan your experiments, assessing multiplexing options. View the excitation and emission spectra for our fluorescent dye range and other commonly used dyes.
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Technical Data for HADA
| M. Wt | 328.71 |
| Formula | C13H12N2O6.HCl |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 2253733-10-5 |
| PubChem ID | 137919867 |
| InChI Key | PLVOEKQNBIXHDI-SBSPUUFOSA-N |
| Smiles | N[C@@H](C(O)=O)CNC(C1=CC(C=CC(O)=C2)=C2OC1=O)=O.Cl |
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 HADA
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 32.87 | 100 |
Preparing Stock Solutions for HADA
The following data is based on the product molecular weight 328.71. 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 | 3.04 mL | 15.21 mL | 30.42 mL |
| 5 mM | 0.61 mL | 3.04 mL | 6.08 mL |
| 10 mM | 0.3 mL | 1.52 mL | 3.04 mL |
| 50 mM | 0.06 mL | 0.3 mL | 0.61 mL |
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Product Datasheets for HADA
References for HADA
References are publications that support the biological activity of the product.
Kuru et al (2012) In Situ probing of newly synthesized peptidoglycan in live bacteria with fluorescent D-amino acids. Angew.Chem.Int.Ed. 51 12519 PMID: 23055266
Hsu et al (2017) Full color palette of fluorescent d-amino acids for in situ labeling of bacterial cell walls. Chem.Sci. 8 6313 PMID: 28989665
Botella et al (2017) Distinct spatiotemporal dynamics of peptidoglycan synthesis between Mycobacterium smegmatis and Mycobacterium tuberculosis. Mbio. 8 e01183 PMID: 28900018
If you know of a relevant reference for HADA, please let us know.
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Keywords: HADA, HADA supplier, fluorescent, D-amino, acid, FDAA, peptidoglycans, labeling, bacteria, labels, labelling, blue, Unnatural, Amino, Acids, Fluorescent, Probes, for, Imaging, Bacteria, 6647, Tocris Bioscience
4 Citations for HADA
Citations are publications that use Tocris products. Selected citations for HADA include:
Baranowski et al (2018) Maturing Mycobacterium smegmatis peptidoglycan requires non-canonical crosslinks to maintain shape. ELife 7 PMID: 30324906
Garcia-Heredia et al (2018) Peptidoglycan precursor synthesis along the sidewall of pole-growing mycobacteria ELife 7 PMID: 30198841
Mariana et al (2022) The Staphylococcus aureus cell division protein, DivIC, interacts with the cell wall and controls its biosynthesis. Commun Biol 5 1228 PMID: 36369270
Marc et al (2021) Single-cell growth inference of Corynebacterium glutamicum reveals asymptotically linear growth. Elife 10 PMID: 34605403
Do you know of a great paper that uses HADA from Tocris? Please let us know.
Reviews for HADA
Average Rating: 5 (Based on 1 Review.)
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Great for labelling bacterial cell walls..
By
Patrick Moynihan on 05/11/2020
Assay Type: In Vitro
Species: Other
We use this product to label the peptidoglycan of growing mycobacterial species. We generally follow published protocols for this, of which there are several. This will label regions of active peptidoglycan synthesis in the cell.
Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
Fluorescent Dyes and Probes Research Product Guide
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