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A1632

Sigma-Aldrich

DL-7-Azatryptophan hydrate

≥98% (TLC)

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About This Item

Empirical Formula (Hill Notation):
C10H11N3O2 · H2O
CAS Number:
7146-37-4
Molecular Weight:
223.23
MDL number:
MFCD00150525
UNSPSC Code:
12352209
PubChem Substance ID:
24890571
NACRES:
NA.26

product name

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Vasant Muralidharan et al.
Journal of the American Chemical Society, 126(43), 14004-14012 (2004-10-28)
An integrated approach is described that allows the domain-specific incorporation of optical probes into large recombinant proteins. The strategy is the combination of two existing techniques, expressed protein ligation (EPL) and in vivo amino acid replacement of tryptophans with tryptophan
Vincenzo De Filippis et al.
Protein science : a publication of the Protein Society, 13(6), 1489-1502 (2004-05-21)
7-Azatryptophan (AW), a noncoded isostere of tryptophan (W), possesses interesting spectral properties. In particular, the presence of a nitrogen atom at position 7 in the indolyl nucleus of AW results in a red shift of the absorption maximum and fluorescence
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Chromatograms

application for HPLC

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