73259-81-1

Basic information

• Product Name: N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid
• Synonyms: Boc-Dapa-OH;Nα-Boc-L-2,3-diaminopropionic acid≥ 98% (HPLC);3-AMINO-(TERT-BUTOXYCARBONYL)-L-ALANINE;L-ALANINE, 3-AMINO-N-[(1,1-DIMETHYLETHOXY)CARBONYL]-;BOC-L-DAP-OH;BOC-L-DAPA-OH;BOC-L-2,3-DIAMINOPROPIONIC ACID;BOC-L-ALPHA,BETA-DIAMINOPROPIONIC ACID
• CAS NO: 73259-81-1
• Molecular Formula: C₈H₁₆N₂O₄
• Molecular Weight: 204.22
• EINECS: 1533716-785-6
• Product Categories: Amino Acids
• Mol File: 73259-81-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 210 °C (dec.)
• Boiling Point: 364.4 °C at 760 mmHg
• Flash Point: 174.2 °C
• Appearance: white powder
• Density: 1.189 g/cm³
• Vapor Pressure: 2.64E-06mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: Store at RT.
• Solubility: DMSO (Slightly, Heated, Sonicated), Water (Sparingly, Heated, Sonicated)
• PKA: 2.88±0.16(Predicted)
• BRN: 4182136
• CAS DataBase Reference: N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid(73259-81-1)
• EPA Substance Registry System: N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid(73259-81-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 73259-81-1(Hazardous Substances Data)

Usage

Description

N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid is a white powder chemical compound that serves as a crucial reactant in various synthetic molecular recognition motifs and protein assembly processes. It plays a significant role in the solid phase synthesis of different bioactive compounds, including antibiotics, hemolytic agents, and peptidic receptor agonists.

Uses

Used in Pharmaceutical Industry:
N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid is used as a reactant for the solid phase synthesis of gramicidin S cyclic analogs, which possess antibiotic and hemolytic activities. These analogs are essential in the development of new antibiotics to combat drug-resistant bacteria and in the study of membrane permeability and ion channels.
N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid is also used as a reactant in the synthesis of HCV protease inhibitor modified analogs. These analogs are vital in the development of antiviral drugs targeting Hepatitis C virus, a significant global health concern.
Used in Peptide Synthesis:
In the field of peptide synthesis, N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid is used as a reactant for the solid phase synthesis of peptidic V1a receptor agonists. These agonists are crucial in the study and treatment of various physiological processes and disorders, including water and electrolyte balance, blood pressure regulation, and stress response.
N-alpha-L-(Butoxycarbonyl)-2,3-diaminopropionic acid is also used for directed peptide assembly at the lipid-water interface. This application is essential in the study of membrane proteins, their interactions, and the development of novel drug delivery systems and targeted therapies.

InChI:InChI=1/C8H16N2O4/c1-8(2,3)14-7(13)10-5(4-9)6(11)12/h5H,4,9H2,1-3H3,(H,10,13)(H,11,12)/t5-/m0/s1

Upstream product

• 7536-55-2 N-t-butyloxycarbonyl-D-asparagine 
• 225780-77-8 2-(R)-(tert-butoxycarbonyl)-amino-3-azidopropionic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 98541-64-1 (2-Oxo-oxetan-3-yl)-carbamic acid tert-butyl ester 
• 98541-64-1 (2-Oxo-oxetan-3-yl)-carbamic acid tert-butyl ester 

Downstream Products

• 61040-22-0 N^β-benzyloxycarbonyl-N^α-Boc-(R)-β-aminoalanine methyl ester 
• 131570-56-4 (R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)propanoic acid 
• 219325-45-8 Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl ester 
• 219325-44-7 benzoic acid 1-[2-(5-bromo-1H-indol-3-yl)-1-(9H-fluoren-9-ylmethoxycarbonyl)-ethylcarbamoyl]-2-{2-[2-tert-butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-3-carbamoyl-propionylamino}-ethyl ester 
• 209223-32-5 (R)-(-)-2-tert-butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid 
• 348081-41-4 (R)-2-tert-butoxycarbonylamino-3-(phenylmethanesulfonylamino)-propionic acid 
• 72071-28-4 (R)-2-tert-butoxycarbonylamino-3-(toluene-4-sulfonylamino)-propionic acid 
• 1237004-93-1 N-(tert-butoxycarbonyl)-3-[(4-fluoro-2-nitrophenyl)amino]-D-alanine 
• 81306-93-6 N²-tert-butoxycarbonyl-N³-benzyloxycarbonyl-D-2,3-diaminopropanoic acid 
• 1429555-68-9 C₂₃H₄₂N₄O₅ 
• 1429555-43-0 C₂₃H₃₆N₄O₅ 
• 159652-30-9 (R)-2,3-bis-tert-butoxycarbonylaminopropionic acid 
• 252209-91-9 (R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine 
• 209223-73-4 (R)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine 

Relevant articles and documents

High-efficiency preparation method of D-dencichine

The invention relates to a high-efficiency synthesis method of a hemostasis compound D-dencichine, comprising the following steps: firstly enabling D-serine to react with di-tert-butyl dicarbonate ester to generate Boc-D-serine, then generating Gabriel reaction with hydroxy of methylsulfonyl chloride activated Boc-D--serine to obtain N-alpha-Boc-D-alpha, beta-diaminopro, finally condensing with oxalate mono-methyl ester sylvite then performing hydrolytic acidification to obtain a dencichine crude product, and purifying to obtain a dencichine competitive product, with the product content reaching more than 99.8%. Compared with existing D-dencichine synthesis methods, the reaction condition is more mild, the operation is simple and convenient, the material cost is relatively low, and the hemostasis compound D-dencichine is environment-friendly, is suitable for industrial production, and solves the problem of resource for later development of clinical trial of D-dencichine.

Aminomethylene peptide nucleic acid (am -PNA): Synthesis, regio-/stereospecific DNA binding, and differential cell uptake of (α/γ, R / S) am- PNA analogues

Inherently chiral, cationic am-PNAs having pendant aminomethylene groups at α(R/S) or γ(S) sites on PNA backbone have been synthesized. The modified PNAs are shown to stabilize duplexes with complementary cDNA in a regio- and stereo-preferred manner with γ(S)-am PNA superior to α(R/S)-am PNAs and α(R)-am PNA better than the α(S) isomer. The enhanced stabilization of am-PNA:DNA duplexes is accompanied by a greater discrimination of mismatched bases. This seems to be a combined result of both electrostatic interactions and conformational preorganization of backbone favoring the cDNA binding. The am-PNAs are demonstrated to effectively traverse the cell membrane, localize in the nucleus of HeLa cells, and exhibit low toxicity to cells.

Novel inhibitors of procollagen C-terminal proteinase. Part 1: Diamino acid hydroxamates

The parallel synthesis of novel inhibitors of procollagen C-terminal proteinase is described. The synthetic strategy allowed for the facile synthesis of a large number of side-chain diversified diamino acid hydroxamates, of which the D-diaminopropionic acid derivatives were shown to be single digit nanomolar PCP inhibitors.