942518-20-9

Basic information

• Product Name: (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID
• Synonyms: (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID;FMOC-AZH-OH;FMOC-L-AZIDOHOMOALANINE;(2S)-N-FMoc-4-azido-butanoic acid;FMoc-γ-azido-Abu-OH;FMoc-Azh;FMoc-azidohoMoalanine;FMoc-Dab(N2)-OH, FMoc-L-g-azidohoMoalanine, FMoc-g-Aha-OH
• CAS NO: 942518-20-9
• Molecular Formula: C₁₉H₁₈N₄O₄
• Molecular Weight: 366.37
• Product Categories: Fmoc Amino Acids;Fmoc-Amino Acids;amino acids
• Mol File: 942518-20-9.mol

Chemical Properties

• Melting Point: 124.0 to 128.0 °C
• Appearance: /
• Storage Temp.: ?20°C
• CAS DataBase Reference: (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID(942518-20-9)
• EPA Substance Registry System: (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID(942518-20-9)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• WGK Germany: 3
• Hazardous Substances Data: 942518-20-9(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID is used as a key intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into the molecular structures of potential drug candidates. Its unique functional groups facilitate the creation of new chemical entities with specific therapeutic properties.
Used in Bioconjugation:
In the field of bioconjugation, (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID serves as a versatile linker or building block for the attachment of biologically active molecules to other entities, such as targeting ligands or imaging agents. This enhances the functionality of bioconjugates for applications in diagnostics, therapeutics, and drug delivery.
Used in the Development of Novel Materials:
(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID is also utilized in material science as a component in the design and synthesis of new materials with tailored properties. Its incorporation into polymers or other materials can lead to advancements in areas such as sensors, coatings, or advanced therapeutic delivery systems.
Further research is essential to fully explore the wide-ranging potential applications of (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID, as its unique structural features and functional groups offer numerous opportunities for innovation across various scientific and industrial domains.

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 120042-14-0 (2S)-2-amino-4-azidobutanoic acid 
• 161420-87-7 N_α-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid 
• 71989-20-3 N₂-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine 
• 125238-99-5 (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid 

Downstream Products

• 1217266-33-5 Nα-Ac-Lys-Gly-hAla(γ-N3)-Ser-Ile-Gln-Nle(δ-yl)-Leu-Arg-NH2 
• 1217266-34-6 Nα-Ac-Lys-Gly-Nle(δ-yl)-Ser-Ile-Gln-hAla(γ-N3)-Leu-Arg-NH2 

Relevant articles and documents

Reagent-Based Diversity-Oriented Synthesis of Triazolo[1,5- A[[1,4]diazepine Derivatives from Polymer-Supported Homoazidoalanine

Herein, we report the synthesis of skeletally different triazolo[1,5-a][1,4]diazepines starting from immobilized homoazidoalanine. After sulfonylation with 2/4-nitrobenzenesulfonyl chlorides and Mitsunobu alkylation with various alkynols, the corresponding N-substituted nitrobenzenesulfonamides were obtained. Their catalyst-free Huisgen cycloaddition provided immobilized and functionalized triazolo[1,5-a][1,4]diazepines as the key intermediates for further modification. Using the concept of diversity-oriented, reagent-based synthesis, the key intermediates were subsequently converted to heterocycles bearing [5 + 7 + 5], [5 + 7 + 6], and [5 + 7 + 7] scaffolds. Furthermore, the synthesis of spirocyclic triazolodiazepines was developed.

Total and Semisyntheses of Polymyxin Analogues with 2-Thr or 10-Thr Modifications to Decipher the Structure-Activity Relationship and Improve the Antibacterial Activity

Herein, we report the total and semisyntheses of a series of polymyxin analogues with 2-Thr and 10-Thr modifications to reveal the structure-activity relationship (SAR), which has not been fully elucidated previously. We employed two total-synthetic strategies to facilitate the diversified replacements on 2-Thr or 10-Thr, respectively. Moreover, semisynthetic approaches were utilized to achieve selective esterification of 2-Thr or dual esterification of both 2- and 10-Thr. Based on the results of in vitro antibacterial assays, SAR analysis implicated that the replacement of 2-/10-Thr with amino acids carrying hydrophobic side chains can maintain the activity against Pseudomonas aeruginosa but had varied effects on other tested Gram-negative bacteria. The aminoacetyl esterification on 2-/10-Thr achieved excellent antibacterial activity, and the compound 76 exhibited 2-8-fold higher activity against different strains and lower toxicity toward the HK-2 cell line. This work explored the SAR of polymyxin 2-/10-Thr and provided a promising strategy for the development of novel polymyxin derivatives.

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

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.

Development of Cell-Permeable, Non-Helical Constrained Peptides to Target a Key Protein–Protein Interaction in Ovarian Cancer

There is a lack of current treatment options for ovarian clear cell carcinoma (CCC) and the cancer is often resistant to platinum-based chemotherapy. Hence there is an urgent need for novel therapeutics. The transcription factor hepatocyte nuclear factor

Efficient synthesis of Fmoc-protected azido amino acids

The efficient two-step synthesis of Fmoc-protected L-azidoalanine and L-azidohomoalanine from readily available Fmoc-protected asparagine and glutamine, respectively, is reported. The synthetic route proceeds in good yield, requires no extra purification steps, and can be carried out on gram scale. The resulting azido amino acids are of sufficient purity for solid-phase peptide synthesis, as demonstrated in the synthesis of a model pentapeptide. Georg Thieme Verlag Stuttgart New York.

Maintaining biological activity by using triazoles as disufide bond mimetics

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

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