905857-46-7

Basic information

• Product Name: (2S)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid
• CAS NO: 905857-46-7
• Molecular Formula: C₂₃H₂₇NO₅
• Molecular Weight: 397.4642
• Mol File: 905857-46-7.mol
• Article Data: 1

Chemical Properties

• Refractive Index: 1.57
• CAS DataBase Reference: (2S)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid(905857-46-7)
• EPA Substance Registry System: (2S)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid(905857-46-7)

Safety Data

• Hazardous Substances Data: 905857-46-7(Hazardous Substances Data)

Usage

Description

(2S)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid, also known as Boc-Glu(OFm)-OH, is a chemical compound with a molecular formula of C28H31NO6 and a molecular weight of 477.55 g/mol. It is a derivative of glutamic acid, featuring a tert-butyloxy group and a fluorenylmethoxy group that protect the amine and carboxylic acid functional groups, respectively. (2S)-2-tert-Butyloxy-4-(9-fluorennylmethoxy)-carbonylaminobutyric Acid plays a crucial role in peptide chemistry and drug discovery, enabling selective protection and deprotection of amino acid residues during peptide synthesis.

Uses

Used in Pharmaceutical Industry:
Boc-Glu(OFm)-OH is utilized as a protectant in the synthesis of peptides, specifically for the selective protection of the amine and carboxylic acid functional groups. This selective protection is essential for the successful synthesis of complex peptide structures and contributes to the development of novel pharmaceuticals and therapeutic agents.
Used in Peptide Chemistry:
In peptide chemistry, Boc-Glu(OFm)-OH serves as an important tool for the synthesis of peptides. Its ability to protect specific functional groups allows for the controlled assembly of peptide chains, facilitating the creation of well-defined and biologically active peptides.
Used in Drug Discovery:
Boc-Glu(OFm)-OH is employed in drug discovery processes to aid in the development of new therapeutic agents. Its role in peptide synthesis enables the production of potential drug candidates with specific biological activities, contributing to the advancement of medicinal chemistry and the discovery of innovative treatments.

Upstream product

• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 905857-44-5 (2S)-2-tert-butyloxy-4-(9-fluorenylmethoxy)carbonylaminobutyrate tert-butyl ester 
• 898529-38-9 (S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-hydroxybutyric acid 
• 905857-45-6 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.