Disease relevance of N-Acetyl-D-tryptophan

• At onset of phototherapy 30 infants received 1 g human serum albumin per kg body weight as a 9% solution containing sodium caprylate and N-acetyltryptophan as stabilizers [1].

Psychiatry related information on N-Acetyl-D-tryptophan

• Slow wave sleep (SWS) was enhanced after SP was microinjected into bilateral vLPO, while SP receptor antagonist, N-acetyl-l-tryptophan 3,5-bis(trifluoromethyl)-benzyl ester, led to the opposite effect [2].

High impact information on N-Acetyl-D-tryptophan

• Human serum albumin (HSA) is found to contain one primary binding site for medium chain fatty acids which is competitive with the binding of N-acetyl-L-tryptophan [3].
• A comparative study of the effect of L-tryptophan and its acetylated derivative N-acetyl-L-tryptophan on rat muricidal behavior [4].
• Purified peptidyl dipeptidase (angiotensin I converting enzyme or kininase II) from human lung or hog kidney is inhibited by commercially prepared plasma protein preparations, by human serum albumin and by the additive albumin stabilizer, acetyltryptophan [5].
• G25K peptides containing an N-terminal N-acetyltryptophan group were studied because their binding to membranes containing a trace of dansylated phospholipid could be detected by fluorescence resonance energy transfer [6].
• The 3,5-bis(trifluoromethyl)benzyl ester of N-acetyl-L-tryptophan (3), which was derived from the screening lead N-ethyl-L-tryptophan benzyl ester, has been used as a starting point to identify high-affinity substance P receptor antagonists with improved in vivo activity [7].

Biological context of N-Acetyl-D-tryptophan

• The pH dependence for acylation of alpha-chymotrypsin by N-acetyltryptophan p-nitrophenyl-, p-nitrothiophenyl-, ethyl-, and thiolethyl esters has been studied by the stopped-flow technique [8].
• Equilibrium sedimentation studies in the absence of inhibitor yielded a dimerization constant of 3.5 L/g. This value was confirmed by frontal gel chromatography of the enzyme on Bio-Gel P-30, which was also used to establish that N-acetyl-L-tryptophan binds preferentially to monomeric enzyme [9].
• Nutritive value of N-acetyl-L-tryptophan in man [10].
• A study of structure-activity relationships of a series of L-tryptophan derivative NK-1 antagonist was performed using 3,5-bis(trifluoromethyl)benzyl ester of N-acetyl-L-Tryptophan (IV) as a starting point [11].

Associations of N-Acetyl-D-tryptophan with other chemical compounds

• N-Chlorosuccinimide reacts with N-acetyltryptophan in a 1:1 ratio to produce the N-acetyl-2-oxindolealanine--a derivative essentially devoid of fluorescence [12].
• A gradual decrease in fluorescence polarization across the emission spectrum on increase in wavelength has been recorded for a number of proteins and also for tryptophan, N-acetyltryptophan and glycyltryptophan [13].
• The fluorescence and excitation spectra of luliberin (luteinizing hormone-releasing factor) in 0.005 M aqueous ammonium acetate are identical in shape to those of N-acetyltryptophan amide and are related to the indole side chain of Trp3 [14].
• Senktide, an NK3-R agonist, stimulated VP release from HNS explants, but neither a neurokinin 1 receptor antagonist [L732,138 (N-acetyl-L-tryptophan 3,5-bis(tri-fluoromethyl)benzyl ester)] nor two NK3-R antagonists (SB222200 and SB235375) prevented SP-stimulated VP release [15].

Gene context of N-Acetyl-D-tryptophan

• Optimization of substitution on the benzyl ester led to the identification of the 3,5-bis-(trifluoromethyl)benzyl ester of N-acetyl-L-tryptophan 26 as a potent and selective substance P receptor antagonist [16].
• Fatty acids, N-acetyl-L-tryptophan and pasteurization had similar effects on the conformational stability of rHSA and HSA [17].
• Selective ion monitoring of tryptophan, N-acetyltryptophan and kynurenine in human serum. Application to the in vivo measurement of tryptophan pyrrolase activity [18].
• Similar deacetylation of N-acetyltryptophan by acylase III was also observed [19].

References