SBR00070
Coumarin Labeled D-Lysine
Suitable for fluorescent microbial imaging
Synonym(s):
D-Lysine blue, D-Lysine, N6-[(7-hydroxy-2-oxo-2H-1-benzopyran-3-yl)carbonyl]- (ACI), FDAA
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About This Item
Empirical Formula (Hill Notation):
C16H18N2O6
CAS Number:
Molecular Weight:
334.32
UNSPSC Code:
12352209
Recommended Products
Quality Level
form
solid
storage temp.
−20°C
SMILES string
O=C(NCCCC[C@@H](N)C(O)=O)C1=CC2=CC=C(O)C=C2OC1=O
InChI
1S/C16H18N2O6/c17-12(15(21)22)3-1-2-6-18-14(20)11-7-9-4-5-10(19)8-13(9)24-16(11)23/h4-5,7-8,12,19H,1-3,6,17H2,(H,18,20)(H,21,22)/t12-/m1/s1
InChI key
QYOUXTJCRWPQLR-GFCCVEGCSA-N
General description
Bacterial Peptidoglycan is a polymer consisting of sugars and amino acids, a mesh-like rigid layer that forms the cell wall. D-Amino Acids (D-AAs) are metabolically incorporated onto the bacterial cell wall by D,D-transpeptidase and/or L,D-transpeptidase. It was recently discovered that those transpeptidases catalyze the metabolic incorporation of exogenous D-AAs with almost no restriction of the side-chain identity. Modification of a D-AA with molecular fluorophores provides fluorescent d-amino acids that can efficiently label in situ peptidoglycan in diverse bacterial species. Coumarin-labeled D-lysine is a fluorescent derivative of D-lysine that is obtained by a synthetic conjugation of D-lysine to the fluorophore. Coumarin labeled D-lysine has high biocompatibility and suitability for labeling peptidoglycans in live bacteria. Additionally, it can be used in tandem with other stains such as FITC-labeled Alanine (SBR00049) to distinguish between different bacteria. Other compatible products useful for live staining include: Rhodamine B labeled Polymyxin B, FITC Labeled D-Lysine, Alanine or Vancomycin and Dansyl labeled polymyxin B (SBR00036, SBR00050, SBR00049, SBR00028, SBR00029).
Application
Fluorescent labeled D-AAs can be used for many applications including:
- Bacterial cell wall morphology
- Bacterial cell wall formation or remodeling activity
- Bacterial viability/activity
- Identify bacterial activity on surfaces or in substances
- Differentiation between various bacterial strains according to their incorporation profile of different D amino acids and sugars
Analysis Note
- Fluorescent microscopyapplication: Coumarin Labeled D-lysine has excitation/emission wavelength rangeat 360/450 nm.
- The recommended working concentrationin fluorescent microscopy imaging application is between 250µM-500 µM inworking medium
- Aliquots of the DMSO solution can bestored at -20 ⁰C, protected from light for at least one month.
related product
Product No.
Description
Pricing
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
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Sheng Hong et al.
Chemical science, 11(17), 4403-4409 (2020-11-20)
Accumulating evidence indicates that colonized microbes play a crucial role in regulating health and disease in the human body. Detecting microbes should be essential for understanding the relationship between microbes and diseases, as well as increasing our ability to detect
Yen-Pang Hsu et al.
Chemical science, 8(9), 6313-6321 (2017-10-11)
Fluorescent d-amino acids (FDAAs) enable efficient in situ labeling of peptidoglycan in diverse bacterial species. Conducted by enzymes involved in peptidoglycan biosynthesis, FDAA labeling allows specific probing of cell wall formation/remodeling activity, bacterial growth and cell morphology. Their broad application
Helene Botella et al.
mBio, 8(5) (2017-09-14)
Peptidoglycan (PG), a polymer cross-linked by d-amino acid-containing peptides, is an essential component of the bacterial cell wall. We found that a fluorescent d-alanine analog (FDAA) incorporates chiefly at one of the two poles in Mycobacterium smegmatis but that polar
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