74802-08-7

Basic information

• Product Name: N^α-t-butyloxycarbonyl-L-kynurenine
• Synonyms: N^α-t-butyloxycarbonyl-L-kynurenine
• CAS NO: 74802-08-7
• Molecular Weight: 308.334
• Mol File: 74802-08-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N^α-t-butyloxycarbonyl-L-kynurenine(CAS DataBase Reference)
• NIST Chemistry Reference: N^α-t-butyloxycarbonyl-L-kynurenine(74802-08-7)
• EPA Substance Registry System: N^α-t-butyloxycarbonyl-L-kynurenine(74802-08-7)

Safety Data

• Hazardous Substances Data: 74802-08-7(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 16055-80-4 (S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid sulfate 
• 2922-83-0 L-kynurenine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 

Downstream Products

• 128776-36-3 Benzyl 2-(3S-3-<<(1,1-Dimethylethoxy)carbonyl>amino>-2,5-dioxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)-ethanoate 
• 74802-14-5 t-butyloxycarbonyl-L-kynurenylglycyl-L-phenylalanine 2,4,6-trimethylbenzyl ester 
• 74802-15-6 L-kynurenylglycyl-L-phenylalanine 
• 74802-13-4 t-butyloxycarbonyl-L-kynurenylglycine p-nitrophenyl ester 

Relevant articles and documents

Labeling Preferences of Diazirines with Protein Biomolecules

Diazirines are widely used in photoaffinity labeling (PAL) to trap noncovalent interactions with biomolecules. However, design and interpretation of PAL experiments is challenging without a molecular understanding of the reactivity of diazirines with protein biomolecules. Herein, we report a systematic evaluation of the labeling preferences of alkyl and aryl diazirines with individual amino acids, single proteins, and in the whole cell proteome. We find that alkyl diazirines exhibit preferential labeling of acidic amino acids in a pH-dependent manner that is characteristic of a reactive alkyl diazo intermediate, while the aryl-fluorodiazirine labeling pattern reflects reaction primarily through a carbene intermediate. From a survey of 32 alkyl diazirine probes, we use this reactivity profile to rationalize why alkyl diazirine probes preferentially enrich highly acidic proteins or those embedded in membranes and why probes with a net positive charge tend to produce higher labeling yields in cells and in vitro. These results indicate that alkyl diazirines are an especially effective chemistry for surveying the membrane proteome and will facilitate design and interpretation of biomolecular labeling experiments with diazirines.

Syntheses of L-Kynurenine Peptides Conducted Without Masking the Side-Chain Amino Group

Various free L-kynurenine peptides, including an analogue of the opiate agonist leucine-enkephalin, have been synthesized by using the Nα-t-butoxycarbonyl derivative of L-kynurenine as a key precursor.By selecting appropriate mild conventional coupling procedures it was possible to carry out the synthetic operations without having to mask the side-chain amino group in any way, but intramolecular acylation with formation of a seven-membered lactam could be demonstrated under more vigorous conditions.