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SBR00070

Sigma-Aldrich

Coumarin Labeled D-Lysine

Suitable for fluorescent microbial imaging

Synonim(y):

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

Wzór empiryczny (zapis Hilla):
C16H18N2O6
Numer CAS:
1471982-29-2
Masa cząsteczkowa:
334.32
Kod UNSPSC:
12352209
NACRES:
NA.21

Poziom jakości

200

Postać

solid

temp. przechowywania

−20°C

ciąg SMILES

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

Klucz InChI

QYOUXTJCRWPQLR-GFCCVEGCSA-N

Opis ogólny

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).

Zastosowanie

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

Komentarz do analizy

  • 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.
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Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Certyfikaty analizy (CoA)

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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

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
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
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
Felipe Cava et al.
The EMBO journal, 30(16), 3442-3453 (2011-07-28)
Production of non-canonical D-amino acids (NCDAAs) in stationary phase promotes remodelling of peptidoglycan (PG), the polymer that comprises the bacterial cell wall. Impairment of NCDAAs production leads to excessive accumulation of PG and hypersensitivity to osmotic shock; however, the mechanistic
Erkin Kuru et al.
Angewandte Chemie (International ed. in English), 51(50), 12519-12523 (2012-10-12)
Tracking a bug's life: Peptidoglycan (PG) of diverse bacteria is labeled by exploiting the tolerance of cells for incorporating different non-natural D-amino acids. These nontoxic D-amino acids preferably label the sites of active PG synthesis, thereby enabling fine spatiotemporal tracking

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