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SBR00050

Sigma-Aldrich

FITC Labeled D-Lysine

Suitable for bacterial labeling

Synonym(s):

FADL, FDAA

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About This Item

Empirical Formula (Hill Notation):
C27H25N3O7S
Molecular Weight:
535.57
UNSPSC Code:
12352209

Quality Level

200

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.
Fluorescein Labeled D-Lysine is a fluorescent derivative of D-Lysine that is obtained by a synthetic conjugation of D-Lysine to a fluorophore. Fluorescein 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-labelled Alanine, Rhodamine B labelled Polymyxin B, FITC labelled vancomycin and Dansyl labelled polymyxin B (SBR00049, SBR00036, 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 betweenvarious bacterial strains according to their incorporation profile of differentD amino acids and sugars

Analysis Note

  • Fluorescent microscopy application: Fluorescein Labeled D-Lysine has excitation/emission wavelength range at 495 nm/515 nm.
  • The recommended working concentration in fluorescent microscopy imaging application is between 250μM-500 μM in DMSO.
  • 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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