905857-50-3

Basic information

• Product Name: (2R)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid
• Synonyms: (2R)-2-(tert-butoxy)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid;(2R)-2-(1,1-Dimethylethoxy)-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid
• CAS NO: 905857-50-3
• Molecular Formula: C₂₃H₂₇NO₅
• Molecular Weight: 397.4642
• Mol File: 905857-50-3.mol
• Article Data: 1

Chemical Properties

• Refractive Index: 1.57
• CAS DataBase Reference: (2R)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid(905857-50-3)
• EPA Substance Registry System: (2R)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid(905857-50-3)

Safety Data

• Hazardous Substances Data: 905857-50-3(Hazardous Substances Data)

Usage

Description

(2R)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid is a complex amino acid derivative featuring a tert-butyloxy and fluorennylmethoxy substituent, along with a carbonyl and amine functional group. Its intricate molecular structure and diverse functional groups suggest potential applications in various fields such as biochemistry, pharmaceuticals, and material science.

Uses

Used in Biochemical Research:
(2R)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid is used as a research compound for exploring its interactions with biological systems and understanding its potential role in biochemical processes.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (2R)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid is used as a precursor or building block in the synthesis of new drugs, potentially targeting specific diseases or conditions due to its unique structure.
Used in Material Science:
(2R)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid is utilized in material science for the development of novel materials with specific properties, such as improved stability or reactivity, based on its chemical composition and functional groups.
Note: The specific applications mentioned above are hypothetical and provided as examples based on the compound's structure and potential. Further research and development would be necessary to validate these uses.

Upstream product

• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 905857-48-9 (2R)-2-tert-butyloxy-4-(9-fluorenylmethoxy)carbonylaminobutyrate tert-butyl ester 
• 905857-47-8 (2R)-4-[(9-fluorenylmethoxy)carbonylamino]-2-hydroxybutyric acid 
• 905857-49-0 C₂₆H₃₅NO₅Si 

Relevant articles and documents

Discrimination of hairpin polyamides with an α-substituted-γ- aminobutyric acid as a 5′-TG-3′ reader in DNA minor groove

Pyrrole-imidazole (Py-lm) polyamides containing stereospecifically α-amino- or α-hydroxyl-substituted γ-aminobutyric acid as a 5′-TG-3′ recognition element were synthesized by machine-assisted Fmoc solid-phase synthesis. Their binding properties to predetermined DNA sequences containing a core binding site of 5′-TGCNCA-3′/3′- ACGN′GT-5′ (N·N′ = A·T, T·A, G·C, and C·G) were then systematically studied by surface plasmon resonance (SPR). SPR results revealed that the pairing of stereospecifically α-amino-/α-hydroxyl-substituted γ-aminobutyric acids, (R or S)-α,γ-diaminobutyric acid (γRN or γSN) and (R or S)-α-hydroxyl-γ-aminobutyric acid (γRO or γSO), side-by-side with β-alanine (β) in such polyamides significantly influenced the DNA binding affinity and recognition specificity of hairpin polyamides in the DNA minor groove compared with β/β, β/γ, and γ/β pairings. More importantly, the polyamide Ac-lm-γSO-lmPy-γ-lmPyβPy-β-Dp (β/γSO) favorably binds to a hairpin DNA containing a core binding site of 5′-TGCNCA- 3′/3′-ACGN′GT-5′ (N·N′ = A·T) with dissociation equilibrium constant (KD) of 1.9 × 10-7 M over N·N′ = T·A with KD = 3.7 × 10 -6 M, with a 19-fold specificity. By contrast, Ac-lm-γSN-lmPy- γ-lmPyβPy-β-Dp (β/γSN) binds to the above sequence with N·N′ = A·T with KD = 8.7 × 10 -7 M over N·N′ = T·A with KD = 8.4 × 10-6 M, with a 9.6-fold specificity. The results also show that the stereochemistry of the α-substituent, as well as the α-substituent itself may greatly alter binding affinity and recognition selectivity of hairpin polyamides to different DNA sequences. Further, we carried out molecular modeling studies on the binding by an energy minimization method, suggesting that α-hydroxyl is very close to N3 of the 3′-terminal G to induce the formation of hydrogen bonding between hydroxyl and N3 in the recognition event of the polyamide Ac-lm-γSO-lmPy-γ- lmPyβPy-β-Dp (β/γSO) to 5′-TGCNCA-3′/3′- ACGN′GT-5′ (N·N′ = A·T). Therefore, SPR assays and molecular modeling studies collectively suggest that the (S)-α-hydroxyl-γ-aminobutyric acid (γSO) may act as a 5′-TG-3′ recognition unit.