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
• Empirical Formula (Hill Notation): C₁₆H₁₈N₂O₆
• CAS Number: 1471982-29-2
• Molecular Weight: 334.32
• UNSPSC Code: 12352209
• NACRES: NA.21

Properties

• Quality Level: 200
• 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

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable