25691-37-6

Basic information

• Product Name: Boc-L-2,4-diaminobutyric acid
• Synonyms: BOC-ALPHA,GAMMA-DIAMINOBUTYRIC ACID;BOC-L-DAB-OH;BOC-DAB-OH;BOC-L-2,4-DIAMINOBUTYRIC ACID;N-ALPHA-T-BUTOXYCARBONYL-L-ALPHA, GAMMA-DIAMINOBUTYRIC ACID;N-ALPHA-T-BUTYLOXYCARBONYL-L-2,4-DIAMINOBUTYRIC ACID;N-ALPHA-TERT-BUTYLOXYCARBONYL-L-2,4-DIAMINOBUTYRIC ACID;N-ALPHA-BOC-L-2,4-DIAMINOBUTYRIC ACID
• CAS NO: 25691-37-6
• Molecular Formula: C₉H₁₈N₂O₄
• Molecular Weight: 218.25
• EINECS: 1533716-785-6
• Product Categories: pharmacetical;Amino Acids & Deriv.;CHIRAL CHEMICALS
• Mol File: 25691-37-6.mol
• Article Data: 21

Chemical Properties

• Melting Point: 192-194 °C
• Boiling Point: 385.5 °C at 760 mmHg
• Flash Point: 186.9 °C
• Appearance: White to off-white/Powder
• Density: 1.16 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: Store at RT.
• Solubility: Methanol (Sparingly), Water (Slightly)
• PKA: 3?+-.0.10(Predicted)
• BRN: 4745487
• CAS DataBase Reference: Boc-L-2,4-diaminobutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-2,4-diaminobutyric acid(25691-37-6)
• EPA Substance Registry System: Boc-L-2,4-diaminobutyric acid(25691-37-6)

Safety Data

• Hazard Codes: Xi
• Statements: 38-41
• Safety Statements: 26-39
• RIDADR: 3265
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 25691-37-6(Hazardous Substances Data)

Usage

Description

Boc-L-2,4-diaminobutyric acid, also known as Boc-Dab, is an organic compound and a derivative of aminobutyric acid. It is characterized by the presence of a Boc (tert-butyloxycarbonyl) protecting group and two amine groups at the second and fourth positions. Boc-L-2,4-diaminobutyric acid is a key building block in the synthesis of various peptides and pharmaceuticals due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
Boc-L-2,4-diaminobutyric acid is used as a synthetic reagent for the development of somatostatin antagonists. These antagonists are crucial in the treatment of various conditions, including acromegaly, a hormonal disorder characterized by excessive growth hormone secretion, and neuroendocrine tumors.
Additionally, Boc-Dab is utilized in the development of blood coagulation factor Xa inhibitors. These inhibitors play a significant role in the prevention and treatment of thromboembolic disorders, such as deep vein thrombosis and pulmonary embolism, by targeting the coagulation cascade and reducing the risk of blood clot formation.

InChI:InChI=1/C9H18N2O4/c1-9(2,3)15-8(14)11-5-4-6(10)7(12)13/h6H,4-5,10H2,1-3H3,(H,11,14)(H,12,13)

Upstream product

• 3350-20-7 (2S)-4-(benzyloxycarbonyl)amino-2-(tert-butoxycarbonyl)aminobutyric acid 
• 7536-55-2 N-tert-butyloxycarbonylasparagine 
• 13726-85-7 Boc-Gln-OH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 117106-21-5 N^α-t-Boc-N^γ-(9-fluorenylmethyloxycarbonyl)-(L)-2,4-diaminobutyric acid 
• 1758-80-1 L-2,4-diaminobutyrate 
• 131570-57-5 (R)-α-t-butyloxycarbonylamino-γ-(9-fluorenylmethoxy)carbonylaminobutyric acid 
• 92828-64-3 (R)-2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester 
• 133645-53-1 benzyl (2R)-(tert-butoxycarbonyl)amino-4-hydroxybutanoate 
• 61348-28-5 (2R)-5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid 

Downstream Products

• 117106-21-5 N^α-t-Boc-N^γ-(9-fluorenylmethyloxycarbonyl)-(L)-2,4-diaminobutyric acid 
• 3350-20-7 (2S)-4-(benzyloxycarbonyl)amino-2-(tert-butoxycarbonyl)aminobutyric acid 
• 223546-35-8 N^α-t-Boc-N^γ-(N-(9-fluorenylmethyloxycarbonyl)-4-aminomethylbenzoyl)-(L)-2,4-diaminobutyric acid 
• 92235-34-2 (2-oxopyrrolidin-3-(S)-yl)carbamic acid tert-butyl ester 
• 124730-07-0 (S)-4-Benzylamino-2-tert-butoxycarbonylamino-butyric acid 
• 642457-77-0 (S)-4-{[(4R,5S)-5-(6-Amino-purin-9-ylmethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-amino}-2-tert-butoxycarbonylamino-butyric acid 
• 550378-17-1 2-tert-butoxycarbonylamino-4-({4-[5-(2,3-dichloro-phenyl)-2-methyl-2H-pyrazol-3-yl]-piperidine-1-carbonyl}-amino)-butyric acid 
• 913338-47-3 4-[2-(3-acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-propylamino]-2-tert-butoxycarbonylamino-butyric acid 
• 181518-87-6 Boc-Dab(Me₂)-OH 
• 949572-10-5 C₂₆H₂₅SN₃O₈ 

Relevant articles and documents

An Improved Preparation of N2-tert-Butoxycarbonyl- and N 2-Benzyloxycarbonyl-(S)-2,4-diaminobutanoic Acids

Utilizing N-benzyloxycarbonyl- (1a) and N-tert-butoxycarbonyl-(S) -glutamine (1b), a highly efficient and practical method for the synthesis of N2-benzyloxycarbonyl- and N 2-tert-butoxycarbonyl-(S)-2,4-diamino-butanoic acids (2a and 2b) has been developed. Reaction of (S)-glutamine derivatives with iodosobenzene diacetate in a mixture of THF-water at 4°C afforded selectively protected (S)-2,4-diaminobutanoic acids in good yields.

The microenvironment and pKaperturbation of aminoacyl-tRNA guided the selection of cationic amino acids

The proteinogenic lysine (Lys) and arginine (Arg) have multiple methylene groups between α-carbon and the terminal charged centre. Why nature did not select ornithine (Orn), 2,4-diamino butyric acid (Dab) and 2,3-diamino propionic acid (Dpr) with fewer methylene groups in the side chain remains an important question! The propensity of aminoacyl-tRNA (aa-tRNA) model substrates towards self-degradationviaintramolecular lactamization was studied using UV spectroscopy and1H-NMR titration, which showed that Lys and Arg remain stable, and Orn and Dab cyclize to lactam. Hydrophobicity-assisted surface mediated model peptide formation highlighted that the microenvironment and pKaperturbation led to poor regioselectivity (α-aminevs.terminal amine) in Dpr and other non-proteinogenic analogues. The α-selectivity became even poorer in the presence of phosphate, making them ill-suited for peptide synthesis. Superior regioselectivity of the Lys aa-tRNA model substrate suggests that the extra methylene bridge helped nature to separate the microenvironments of the α-amine and ε-amine to synthesize the peptide backbone.

Structural design and synthesis of bimodal PNA that simultaneously binds two complementary DNAs to Form fused double duplexes

Bimodal PNAs are new PNA constructs designed to bind two different cDNA sequences synchronously to form double duplexes. They are synthesized on solid phase using sequential coupling and click reaction to introduce a second base in each monomer at Cα via alkyltriazole linker. The ternary bimodal PNA:DNA complexes show stability higher than that of individual duplexes. Bimodal PNAs are appropriate to create higher-order fused nucleic acid assemblies.