1097192-04-5

Basic information

• Product Name: Fmoc-δ-azido-Nva-OH
• Synonyms: FMOC-L-DELTA-AZIDOORNITHINE;(2S)-N-FMoc-5-azido--Pentenoic acid;5-Azido-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-norvaline;Fmoc-L-Orn(N3)-OH;Fmoc-δ-azido-Nva-OH;FMoc-L-azidoornithine;FMoc-d-azido-Nva-OH;FMoc-Orn(N2)-OH
• CAS NO: 1097192-04-5
• Molecular Formula: C₂₀H₂₀N₄O₄
• Molecular Weight: 380.3972
• Product Categories: amino acids;Unusual Amino Acids
• Mol File: 1097192-04-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Fmoc-δ-azido-Nva-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-δ-azido-Nva-OH(1097192-04-5)
• EPA Substance Registry System: Fmoc-δ-azido-Nva-OH(1097192-04-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 1097192-04-5(Hazardous Substances Data)

Usage

Uses

(S)?-?Fmoc-?2-?amino-?5-?azido-?pentanoic Acid is a chiral reagent used in preparing macrocyclic constraints in peptides (peptide stapling) which is an important tool in medicinal peptide chemistry. in addition, (S)?-?Fmoc-?2-?amino-?5-?azido-?pentanoic Acid has been used in the synthesis of clicked peptides.

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 156463-09-1 2-amino-5-azidopentanoic acid 
• 201046-57-3 N^α-(9-fluorenylmethoxy)carbonyl-L-ornithine hydrochloride 
• 13650-49-2 N^δ-(tert-butoxycarbonyl)-L-ornithine 
• 109425-55-0 Fmoc-Orn(Boc)-OH 
• 173690-58-9 (S)-tert-butyl 2-tert-butoxycarbonylamino-5-methylsulfonyloxypentanoate 
• 90194-99-3 tert-butyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate 
• 24277-39-2 N-tert-butoxycarbonyl glutamic acid tert-butyl ester 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 158599-00-9 (S)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid 

Downstream Products

• 158599-00-9 (S)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid 
• 1217266-28-8 Nα-Ac-Lys-Gly-Nva(δ-N3)-Ser-Ile-Gln-Pra-Leu-Arg-NH2 
• 1217266-30-2 Nα-Ac-Lys-Gly-Pra-Ser-Ile-Gln-Nva(δ-N3)-Leu-Arg-NH2 
• 1217266-36-8 Nα-Ac-Lys-Gly-Nle(δ-yl)-Ser-Ile-Gln-Nva(δ-N3)-Leu-Arg-NH2 

Relevant articles and documents

Identification of a new p53/MDM2 inhibitor motif inspired by studies of chlorofusin

Previous studies on the natural product chlorofusin have shown that the full peptide and azaphilone structure are required for inhibition of the interaction between MDM2 and p53. In the current work, we utilized the cyclic peptide as a template and introd

Water-soluble, stable and azide-reactive strained dialkynes for biocompatible double strain-promoted click chemistry

The Sondheimer dialkyne is extensively used in double strain-promoted azide-alkyne cycloadditions. This reagent suffers with poor water-solubility and rapidly decomposes in aqueous solutions. This intrinsically limits its application in biological systems, and no effective solutions are currently available. Herein, we report the development of novel highly water-soluble, stable, and azide-reactive strained dialkyne reagents. To demonstrate their extensive utility, we applied our novel dialkynes to a double strain-promoted macrocyclisation strategy to generate functionalised p53-based stapled peptides for inhibiting the oncogenic p53-MDM2 interaction. These functionalised stapled peptides bind MDM2 with low nanomolar affinity and show p53 activation in a cellular environment. Overall, our highly soluble, stable and azide-reactive dialkynes offer significant advantages over the currently used Sondheimer dialkyne, and could be utilised for numerous biological applications.

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