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Fmoc-δ-azido-Nva-OH, also known as (S)-Fmoc-2-amino-5-azido-pentanoic acid, is a chiral reagent with a unique azido group that plays a crucial role in the field of medicinal peptide chemistry. It is characterized by its ability to form stable covalent bonds through click chemistry, which allows for the creation of macrocyclic constraints in peptides, enhancing their stability and bioactivity.

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  • (2S)-5-azido-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid

    Cas No: 1097192-04-5

  • USD $ 1.9-2.9 / Gram

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  • 1000 Metric Ton/Month

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  • 1097192-04-5 Structure
  • Basic information

    1. Product Name: Fmoc-δ-azido-Nva-OH
    2. 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
    3. CAS NO:1097192-04-5
    4. Molecular Formula: C20H20N4O4
    5. Molecular Weight: 380.3972
    6. EINECS: N/A
    7. Product Categories: amino acids;Unusual Amino Acids
    8. Mol File: 1097192-04-5.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. CAS DataBase Reference: Fmoc-δ-azido-Nva-OH(CAS DataBase Reference)
    10. NIST Chemistry Reference: Fmoc-δ-azido-Nva-OH(1097192-04-5)
    11. EPA Substance Registry System: Fmoc-δ-azido-Nva-OH(1097192-04-5)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1097192-04-5(Hazardous Substances Data)

1097192-04-5 Usage

Uses

Used in Medicinal Peptide Chemistry:
Fmoc-δ-azido-Nva-OH is used as a chiral reagent for preparing macrocyclic constraints in peptides. This application is crucial for peptide stapling, a technique that improves the stability and bioactivity of peptides, making them more effective as therapeutic agents.
Used in Click Chemistry:
Fmoc-δ-azido-Nva-OH is utilized in the synthesis of clicked peptides, a process that involves the formation of stable covalent bonds through click chemistry. This method allows for the rapid and efficient synthesis of complex peptide structures, which can be further explored for their potential applications in drug discovery and development.

Check Digit Verification of cas no

The CAS Registry Mumber 1097192-04-5 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,9,7,1,9 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1097192-04:
(9*1)+(8*0)+(7*9)+(6*7)+(5*1)+(4*9)+(3*2)+(2*0)+(1*4)=165
165 % 10 = 5
So 1097192-04-5 is a valid CAS Registry Number.

1097192-04-5 Well-known Company Product Price

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  • Aldrich

  • (714291)  (S)-5-Azido-2-(Fmoc-amino)pentanoicacid  ≥97.0% (HPLC)

  • 1097192-04-5

  • 714291-250MG

  • 3,844.62CNY

  • Detail

1097192-04-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-5-azido-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid

1.2 Other means of identification

Product number -
Other names Fmoc-L-|A-azidoornithine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1097192-04-5 SDS

1097192-04-5Relevant articles and documents

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

Cominetti, Marco M.D.,Goffin, Sarah A.,Raffel, Ewan,Turner, Kerrie D.,Ramoutar, Jordann C.,O'Connell, Maria A.,Howell, Lesley A.,Searcey, Mark

, p. 4878 - 4880 (2015)

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

Maintaining biological activity by using triazoles as disufide bond mimetics

Holland-Nell, Kai,Meldal, Morten

, p. 5204 - 5206 (2011)

Click into place: Tachyplesin-I (TP-I) analogues in which both disulfide bridges (1) have been replaced with triazoles (2) represent structural mimetics of TP-I that display similar or slightly improved antibacterial activity. Optimized structures were obtained by replacing the cysteine residues in TP-I by azido- and alkyno-functionalized amino acids. Copyright

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

Sharma, Krishna,Strizhak, Alexander V.,Fowler, Elaine,Wang, Xuelu,Xu, Wenshu,Hatt Jensen, Claus,Wu, Yuteng,Sore, Hannah F.,Lau, Yu Heng,Hyv?nen, Marko,Itzhaki, Laura S.,Spring, David R.

supporting information, p. 8014 - 8018 (2019/09/06)

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.

Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides

Pícha, Jan,Budě?ínsky, Milo?,Machá?ková, Kate?ina,Collinsová, Michaela,Jirá?ek, Ji?í

, p. 202 - 214 (2017/04/06)

The rise of CuI-catalyzed click chemistry has initiated an increased demand for azido and alkyne derivatives of amino acid as precursors for the synthesis of clicked peptides. However, the use of azido and alkyne amino acids in peptide chemistry is complicated by their high cost. For this reason, we investigated the possibility of the in-house preparation of a set of five Fmoc azido amino acids: β-azido l-alanine and d-alanine, γ-azido l-homoalanine, δ-azido l-ornithine and ω-azido l-lysine. We investigated several reaction pathways described in the literature, suggested several improvements and proposed several alternative routes for the synthesis of these compounds in high purity. Here, we demonstrate that multigram quantities of these Fmoc azido amino acids can be prepared within a week or two and at user-friendly costs. We also incorporated these azido amino acids into several model tripeptides, and we observed the formation of a new elimination product of the azido moiety upon conditions of prolonged couplings with 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate/DIPEA. We hope that our detailed synthetic protocols will inspire some peptide chemists to prepare these Fmoc azido acids in their laboratories and will assist them in avoiding the too extensive costs of azidopeptide syntheses. Experimental procedures and/or analytical data for compounds 3–5, 20, 25, 26, 30 and 43–47 are provided in the supporting information.

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

Isaad, Alexandra Le Chevalier,Barbetti, Francesca,Rovero, Paolo,D'Ursi, Anna Maria,Chelli, Mario,Chorev, Michael,Papini, Anna Maria

experimental part, p. 5308 - 5314 (2009/06/18)

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

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