156463-09-1

Basic information

• Product Name: 5-AZIDO-L-NORVALINE
• Synonyms: 5-AZIDO-L-NORVALINE;H-L-Orn(N3)-OH*HCI;D-2-Amino-5-azido-pentanoic acid hydrochloride;H-D-Orn(N3)-OH·HCl;Nδ-Azido-D-Ornithine hydrochloride≥ 99% (HPLC);H-L-Orn(N3)-OH·HCl;L-2-Amino-5-azido-pentanoic acid hydrochloride;L-Azidonorvaline·HCl
• CAS NO: 156463-09-1
• Molecular Formula: C5H10 N4 O2
• Molecular Weight: 0
• Mol File: 156463-09-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-AZIDO-L-NORVALINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AZIDO-L-NORVALINE(156463-09-1)
• EPA Substance Registry System: 5-AZIDO-L-NORVALINE(156463-09-1)

Safety Data

• Hazardous Substances Data: 156463-09-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Upstream product

• 21887-64-9 N₂-(tert-butoxycarbonyl)-L-ornithine 
• 2480-93-5 Boc-Orn(Z)-OH 
• 763139-35-1 5-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}pentanoic acid 
• 1224702-11-7 (S)-benzyl 5-azido-2-(tert-butoxycarbonylamino)pentanoate 
• 161264-04-6 (2R)-N-<(2S)-2-<amino>-5-chloropentan-1-oyl>bornane-10.2-sultam 

Downstream Products

• 1097192-04-5 N^α-(9-fluorenylmethyloxycarbonyl)-azido-L-ornithine 

Relevant articles and documents

A concise route to L-azidoamino acids: L-azidoalanine, L-azidohomo-alanine and L-azidonorvaline

A simple and highly efficient synthetic route to three homologous azidoamino acids, starting from inexpensive, commercially available, protected natural amino acids is reported. The products can be used to introduce bioorthogonal handles into proteins. Ge

Nα-Fmoc-protected ω-azido- and ω-alkynyl-L- amino acids as building blocks for the synthesis of "clickable" peptides

The growing interest in the 1,4-disubstituted-1,2,3-triazolyl moiety as an amide bond surrogate and its formation through very mild, chemoselective, and bioorthogonal CuI-catalyzed Huisgen 1,3-dipolar [3+2] cycloaddition of an alkynyl to an azi

Presentation and detection of azide functionality in bacterial cell surface proteins

An improved protocol for copper-catalyzed triazole formation on the bacterial cell surface is described. Addition of highly pure CuBr to cells treated with azidohomoalanine (2) leads to ca. 10-fold more extensive cell surface labeling than previously observed. This highly active catalyst allows detection of the methionine analogues azidoalanine (1), azidonorvaline (3), and azidonorleucine (4) in cell surface proteins. Azidoalanine was previously believed to be silent with regard to the cellular protein synthesis machinery.

Asymmetric alkylations of a sultam-derived glycine equivalent: Practical preparation of enantiomerically pure α-amino acids

Alkylation of the chiral glycine derivative 2 with 'activated' organohalides under ultrasound-assisted phase-transfer catalysis or with activated and nonactivatcd organohalides in anhydrous medium provides (mostly crystalline) alkylation products 3. Acidic hydrolysis of the pure products 3 gives (aminoacyl)sultams 4 which by mild saponification furnish pure α-amino acids 5 in good overall yields from 2, along with recovered auxiliary 1 (Scheme 1). Pure ω-protected α,ω-diamino acids and α-amino-ω-(hydroxyamino)acids 12-16 are readily accessible from (ω-haloacyl)sultams 3 via reaction with N-nucleophiles followed by acidic and basic hydrolyses (Scheme 2). A reliable determination of the enantiomeric purity of α-amino acids using HPLC analysis of their N-(3,5-dinitrobenzoyl)prolyl derivatives 17 is presented.