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SBR00069

Sigma-Aldrich

Rhodamine labeled D-Lysine

Suitable for fluorescent microbial imaging

Synonym(s):

D-Lysine red, FDAA, TDL

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About This Item

Empirical Formula (Hill Notation):
C31H34N4O6
CAS Number:
Molecular Weight:
558.62
UNSPSC Code:
12352209
NACRES:
NA.21

Quality Level

form

solid

storage temp.

−20°C

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. Rhodamine-Labeled D-lysine (TDL) is a fluorescent derivative of D-lysine that is obtained by a synthetic conjugation of D-lysine to the fluorophore. Rhodamine 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 D-Alanine (SBR00049) to distinguish between different bacteria. Other compatible products useful for live staining include: Rhodamine B Labeled Polymyxin B, FITC Labeled D-Lysine, FITC Labeled Vancomycin and Dansyl Labeled Polymyxin B (SBR00036, SBR00050, SBR00028, SBR00029 and SBR00047).

Application

Fluorescent labeled D-AAs (FDAAs) 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 microscopy application: Rhodamine Labeled D-lysine has excitation/emission wavelength range at 550/570 nm.
  • The recommended working concentration in fluorescent microscopy imaging application is between 250 µM-500 µM in working medium.
  • Aliquots of the DMSO solution can be stored at -20 °C, protected from light for at least one month.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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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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