851909-08-5

Basic information

• Product Name: (S)-N-Fmoc-2-(3'-butenyl)glycine
• Synonyms: (2S)-2-(Fmoc-amino)-5-hexenoic acid;Fmoc-(2S)-2-AMINO-5-HEXENOIC ACID;(S)-N-Fmoc-2-(3'-butenyl)glycine;(2S)-2-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-5-hexenoic acid;(S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)hex-5-enoic acid;(9H-Fluoren-9-yl)MethOxy]Carbonyl L-Homoallylglycine
• CAS NO: 851909-08-5
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351
• EINECS: -0
• Mol File: 851909-08-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 573.744 °C at 760 mmHg
• Flash Point: 300.79 °C
• Appearance: /
• Density: 1.222
• Storage Temp.: 2-8°C
• PKA: 3.85±0.10(Predicted)
• CAS DataBase Reference: (S)-N-Fmoc-2-(3'-butenyl)glycine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Fmoc-2-(3'-butenyl)glycine(851909-08-5)
• EPA Substance Registry System: (S)-N-Fmoc-2-(3'-butenyl)glycine(851909-08-5)

Safety Data

• Hazardous Substances Data: 851909-08-5(Hazardous Substances Data)

Usage

General Description

(S)-N-Fmoc-2-(3'-butenyl)glycine is a specific chemical compound that belongs to the group of amino acids. (S)-N-Fmoc-2-(3'-butenyl)glycine is commonly used in peptide synthesis and is often employed as a building block in the production of peptides and proteins. The "N-Fmoc" in its name indicates that it possesses a fluorenylmethyloxycarbonyl (Fmoc) protecting group, which is important for controlling the reactivity and selectivity of the amino acid during peptide synthesis. The "2-(3'-butenyl)" part of the compound's name suggests the presence of a butenyl functional group at the second position of the molecule, which affects its chemical properties and reactivity. Overall, (S)-N-Fmoc-2-(3'-butenyl)glycine is a crucial component in the synthesis of biologically active peptides and can be used in various research and industrial applications.

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 90989-12-1 (2S)-2-amino-5-hexenoic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 

Downstream Products

• 851909-04-1 N-(N-(Fmoc)-L-homoallylglycyl)-N-(2,4-dimethoxybenzyl)-L-allylglycine methyl ester 
• 851908-96-8 methyl (E,3S,9S)-3-N-(Fmoc)amino-1-(2,4-dimethoxybenzyl)-2-oxo-2,3,4,5,8,9-hexahydro-1H-azonine-9-carboxylate 
• 1186613-29-5 C₈₀H₁₁₂N₇O₁₈P 
• 1312681-99-4 (3S,6R,7S,10S)-methyl 2-oxo-3-N-(Fmoc)amino-6-phenoxy-1-azabicyclo[5.3.0]decane-10-carboxylate 
• 1338002-17-7 N-9-fluorenylmethoxycarbonyl-L-decanylglycine 

Relevant articles and documents

Macrocyclic BACE1 inhibitors with hydrophobic cross-linked structures: Optimization of ring size and ring structure

Based on the X-ray crystallography of recombinant BACE1 and a hydroxyethylamine-type peptidic inhibitor, we introduced a cross-linked structure between the P1 and P3 side chains of the inhibitor to enhance its inhibitory activity. The P1 and P3 fragments bearing terminal alkenes were synthesized, and a ring-closing metathesis of these alkenes was used to construct the cross-linked structure. Evaluation of ring size using P1 and P3 fragments with various side chain lengths revealed that 13-membered rings were optimal, although their activity was reduced compared to that of the parent compound. Furthermore, the optimal ring structure was found to be a macrocycle with a dimethyl branched substituent at the P3 β-position, which was approximately 100-fold more active than the non-substituted macrocycle. In addition, the introduction of a 4-carboxymethylphenyl group at the P1′ position further improved the activity.

Insight into Transannular Cyclization Reactions to Synthesize Azabicyclo[X.Y.Z]alkanone Amino Acid Derivatives from 8-, 9-, and 10-Membered Macrocyclic Dipeptide Lactams

An efficient method for synthesizing different functionalized azabicyclo[X.Y.0]alkanone amino acid derivatives has been developed employing electrophilic transannular cyclizations of 8-, 9-, and 10-membered unsaturated macrocycles to form 5,5-, 6,5-, 7,5-, and 6,6-fused bicylic amino acids, respectively. Macrocycles were obtained by a sequence featuring peptide coupling of vinyl-, allyl-, homoallyl-, and homohomoallylglycine building blocks followed by ring-closing metathesis. X-ray crystallographic analyses of the 8-, 9-, and 10-membered macrocyclic lactam starting materials as well as certain bicyclic amino acid products provided insight into their conformational preferences as well as the mechanism for the diastereoselective formation of specific azabicycloalkanone amino acids by way of transannular iodolactamization reactions. (Chemical Equation Presented).

Prolonged stability by cyclization: Macrocyclic phosphino dipeptide isostere inhibitors of β-secretase (BACE1)

Cyclization of recently reported linear phosphino dipeptide isostere inhibitors of BACE1 via side chain olefin metathesis yielded macrocyclic BACE1 inhibitors. The most potent compound II-P1 (IC50 of 47 nM) and the corresponding linear analog I were tested for serum stability. The approach led to three times prolonged half life serum stability of 44 min for the macrocyclic inhibitor II-P1 compared to the linear compound I.