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MilliporeSigma

A1632

Sigma-Aldrich

DL-7-Azatryptophan hydrate

≥98% (TLC)

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About This Item

Fórmula empírica (notación de Hill):
C10H11N3O2 · H2O
Número de CAS:
Peso molecular:
223.23
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

Nombre del producto

DL-7-Azatryptophan hydrate,

assay

≥98% (TLC)

form

powder

color

white to off-white

storage temp.

−20°C

SMILES string

O.NC(Cc1c[nH]c2ncccc12)C(O)=O

InChI

1S/C10H11N3O2.H2O/c11-8(10(14)15)4-6-5-13-9-7(6)2-1-3-12-9;/h1-3,5,8H,4,11H2,(H,12,13)(H,14,15);1H2

InChI key

PXDRHYQAIUZKHN-UHFFFAOYSA-N

Biochem/physiol Actions

DL-7-Azatryptophan is a racemic mixture of D- and L-7-azatryptophan which together with L-tryptophan is a synergistic inducer of tryptophan oxygenase of Pseudomonas acidovorans. DL-7-Azatryptophan inhibits photosynthetic carbon assimilation, photosynthetic oxygen evolution and nitrogen metabolism in Anabaena sp. Strain 1F, a marine filamentous, heterocystous cyanobacterium.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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P Cioni et al.
Biochemical and biophysical research communications, 248(2), 347-351 (1998-07-24)
The tryptophan analogues 7-azaindole (7-Aza W) and 5-hydroxytryptophan (5-OH W) have a significant absorbance between 310-320 nm, which allows them to act as selective luminescence probes in protein mixtures containing a large number of tryptophan residues. To assess the potential
P Soumillion et al.
Protein engineering, 8(5), 451-456 (1995-05-01)
The phage lambda lysozyme (lambda L) contains four tryptophans. These have been efficiently replaced by 7-azatryptophan (7aW) through biosynthetic incorporation into the overexpressed protein. Comparative analysis of the effect of temperature or pH on the fluorescence of the wild-type lambda
H Rosenfeld et al.
Journal of bacteriology, 97(2), 697-704 (1969-02-01)
The process of induction of tryptophan oxygenase in Pseudomonas acidovorans is typical of many microbial enzyme induction systems, in that it (i) requires cell multiplication and de novo protein synthesis, (ii) is subject to catabolite repression, (iii) results in the
C H Chen et al.
Journal of bacteriology, 169(3), 1107-1113 (1987-03-01)
The addition of DL-7-azatryptophan (AZAT), a tryptophan analog, to continuous cultures of Anabaena sp. strain CA grown with 10 mM nitrate as the nitrogen source resulted in the differentiation of heterocysts. Analysis of the intracellular amino acid pools of Anabaena
Julie M G Rogers et al.
Analytical biochemistry, 399(2), 182-189 (2009-12-29)
Fluorescence resonance energy transfer (FRET) provides a powerful means to study protein conformational changes. However, the incorporation of an exogenous FRET pair into a protein could lead to undesirable structural perturbations of the native fold. One of the viable strategies

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