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SBR00049

Sigma-Aldrich

FITC Labeled D-Alanine

Suitable for bacterial labeling

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About This Item

Empirical Formula (Hill Notation):
C24H19N3O7S
Molecular Weight:
493.49
UNSPSC Code:
12352209
NACRES:
NA.24

Quality Level

200

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.
Fluorescein Labeled D-Alanine is a fluorescent derivative of D-alanine that is obtained by a synthetic conjugation of 3-amino-D-alanine to a fluorophore. Fluorescein Labeled D-Alanine has high biocompatibility and suitability for labeling peptidoglycans in live bacteria

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

Analysis Note

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