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Cat.No. 6647 - HADA | C13H12N2O6.HCl | CAS No. 2253733-10-5
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)
Citations (2)
Reviews (1)
Literature (1)

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.

Applications for HADA

Application of HADA

Figure 1: Investigating mycobacteria cell wall formation using FDAA HADA. Image showing FDAA HADA incorporation in log-phase growth of WT, Δ L,D-transpeptidases (LDT) and Δ 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

Application of RADA

Figure 2: Using FDAAs HADA and RADA (Cat. No 6649) 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 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

Optical Data for HADA

HADA Dye Spectra
Emission Color Blue
λabs 405 nm
λem 450 nm
Extinction Coefficient (ε) 36,700 M-1cm-1

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
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
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.

Select a batch to recalculate based on the batch molecular weight:
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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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.

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

2 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

Do you know of a great paper that uses HADA from Tocris? Please let us know.

Reviews for HADA

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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.

review image

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.

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