214475-53-3

Usage

Chemical Properties

White to off-white powder

Synthetic route

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 4-Hydrazinobenzoic acid (619-67-0) → 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3)

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane	75%

(S)-2-Amino-3-(4-chloro-phenyl)-propionic acid benzhydryl ester + 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → (S)-3-(4-Chloro-phenyl)-2-{4-[N'-(9H-fluoren-9-ylmethoxycarbonyl)-hydrazino]-benzoylamino}-propionic acid benzhydryl ester

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 48h; Ambient temperature;

4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → (S)-3-(4-Chloro-phenyl)-2-{4-[N'-(9H-fluoren-9-ylmethoxycarbonyl)-hydrazino]-benzoylamino}-propionic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: DCCI, HOBt / dimethylformamide / 48 h / Ambient temperature 2: TFA, anisole / 2.5 h / Ambient temperature View Scheme

taxol (33069-62-4) + 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → C69H67N3O17

Conditions	Yield
With dmap; diisopropyl-carbodiimide In DMF (N,N-dimethyl-formamide)

polyethylene glycol polyamide resin + 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → C22H18N3O3Pol

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 13h; Inert atmosphere; solid phase reaction;

Fmoc-Val-OH (68858-20-8) + Fmoc-Leu-OH (35661-60-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + C26H25N6O5Pol + C50H45NO15 (1571865-26-3) + N-Fmoc L-Phe (35661-40-6) + 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → C68H74N7O16Pol

Conditions

Yield

Stage #1: C26H25N6O5Pol With piperidine In N,N-dimethyl-formamide Stage #2: 4-(Fmoc-hydrazino)-benzoic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide TenGel NH2 resin; Stage #3: Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; C50H45NO15; N-Fmoc L-Phe Further stages;

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 619-67-0 4-Hydrazinobenzoic acid 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Relevant academic research and scientific papers

Chemoselective Copper-Mediated Modification of Selenocysteines in Peptides and Proteins

Highly valuable bioconjugated molecules must be synthesized through efficient, chemoselective chemical modifications of peptides and proteins. Herein, we report the chemoselective modification of peptides and proteins via a reaction between selenocysteine residues and aryl/alkyl radicals. In situ radical generation from hydrazine substrates and copper ions proceeds rapidly in an aqueous buffer at near neutral pH (5-8), providing a variety of Se-modified linear and cyclic peptides and proteins conjugated to aryl and alkyl molecules, and to affinity label tag (biotin). This chemistry opens a new avenue for chemical protein modifications.

Aryl hydrazides as linkers for solid phase synthesis which are cleavable under mild oxidative conditions

We have developed an acid/base stable aryl hydrazide linker which is readily coupled to solid phase resins. Cleavage is specific and facile, requiring a copper (II) catalyst, base and a nucleophile to proceed. The conditions are compatible with all 20 proteinogenic amino acids and quantitative cleavage is achieved within 2 hours at 20°C to give peptides with C-terminal acid, amide or ester functionalities. Aryl hydrazides also offer scope as simple 'traceless' linkers.