4033-39-0

Basic information

• Product Name: L-2,3-Diaminopropionic acid
• Synonyms: L-2,3-Diaminopropionic acid;L-Dap;(2S)-2,3-diaminopropanoic acid;H-Dap-OH;(2S)-2,3-Diaminopropionic acid;(S)-2,3-Diaminopropionic acid;[S,(+)]-2,3-Diaminopropionic acid;L-2,3-Diaminopropion
• CAS NO: 4033-39-0
• Molecular Formula: C₃H₈N₂O₂
• Molecular Weight: 104.11
• Mol File: 4033-39-0.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 325.615 °C at 760 mmHg
• Flash Point: 150.727 °C
• Appearance: /
• Density: 1.295 g/cm³
• Vapor Pressure: 4.58E-05mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.76±0.10(Predicted)
• CAS DataBase Reference: L-2,3-Diaminopropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: L-2,3-Diaminopropionic acid(4033-39-0)
• EPA Substance Registry System: L-2,3-Diaminopropionic acid(4033-39-0)

Safety Data

• Hazardous Substances Data: 4033-39-0(Hazardous Substances Data)

Usage

General Description

L-2,3-Diaminopropionic acid is a non-proteinogenic amino acid that contains two amino groups and a carboxylic acid functional group. It is also known as α,β-diaminopropionic acid and is classified as a beta-amino acid. L-2,3-Diaminopropionic acid is not commonly found in nature but can be synthesized in a laboratory setting. L-2,3-Diaminopropionic acid is of interest in the field of pharmaceuticals and drug development due to its potential therapeutic properties. Research has shown that it may have neuroprotective effects and could be used in the treatment of neurodegenerative diseases. Additionally, it has been studied for its potential role in the synthesis of peptide-based drugs and as a building block in organic chemistry.

InChI:InChI=1/C3H8N2O2/c4-1-2(5)3(6)7/h2H,1,4-5H2,(H,6,7)/t2-/m0/s1

Upstream product

• 62234-28-0 N^α-Tos-D-A₂pr 
• 1783-96-6 (2R)-aspartic acid 
• 20584-70-7 L-3-acetyl-amino-2-amino-propionic acid 
• 515-94-6 2,3-diaminopropanoic acid 
• 56-84-8 L-Aspartic acid 
• 194427-76-4 (11S)-cyclocinamide A 
• 70-47-3 L-asparagine 
• 1356449-88-1 calyxamide B 
• 1356449-87-0 calyxamide A 
• 5302-45-4 b-oxalylamino-L-alanine 
• 112317-44-9 deglycobleomycin-A₂ 
• 11116-31-7 bleomycin-A₂ 
• 35761-26-3 (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid 
• 75452-33-4 Boc-Dap(NH₂)-CONH₂ 

Downstream Products

• 1483-07-4 L-2-Amino-3-ureido-propanoic acid 
• 88971-40-8 N^α,N^β-bis(t-butoxycarbonyl)-L-α,β-diaminopropionic acid 
• 65621-26-3 (S)-N,N'-dicarbobenzyloxy-2,3-diaminopropanoic acid 
• 1226758-32-2 N',N',Nα-tris(cyanoethyl)-L-α,β-diaminopropionic acid 
• 1226758-34-4 Nα,N',Nα,N'-tetrakis(cyanoethyl)-L-α-diaminopropionic acid 
• 686259-72-3 C₄H₁₀N₂O₂ 
• 20610-20-2 methyl (S)-2,3-diaminopropanoate 
• 76387-70-7 (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid 
• 1389347-69-6 (S)-2,3-distearamidopropanoic acid 
• 161372-39-0 L-2,3-diaminopropionic acid methyl ester hydrochloride 
• 6059-44-5 (L)-2,3-diaminopropionic acid methyl ester dihydrochloride 
• 1452144-89-6 C₁₀H₁₈N₄O₆S 
• 159652-30-9 (R)-2,3-bis-tert-butoxycarbonylaminopropionic acid 
• 802294-64-0 propionic acid 

Relevant articles and documents

Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle Silpha perforata

Coprisamides C and D (1 and 2) were isolated from a gut bacterium, Micromonospora sp. UTJ3, of the carrion beetle Silpha perforata. Based on the combined analysis of UV, MS, and NMR spectral data, the planar structures of 1 and 2 were elucidated to be unreported derivatives of coprisamides A and B, cyclic depsipeptides bearing a 2-alkenylcinnamic acid unit and the unusual amino acids β-methylaspartic acid and 2,3-diaminopropanoic acid. The absolute configuration of 1 was determined using the advanced Marfey's method, phenylglycine methyl ester derivatization, and J-based configuration analysis. The biosynthetic gene clusters for the coprisamides were investigated based on genomic data from coprisamide-producing strains Micromonospora sp. UTJ3 and Streptomyces sp. SNU533. Coprisamide C (1) was active against the Mycobacterium tuberculosis mc26230 strain.

Synthesis of L-2,3-diaminopropionic acid, a siderophore and antibiotic precursor

L-2,3-diaminopropionic acid (L-Dap) is an amino acid that is a precursor of antibiotics and staphyloferrin B a siderophore produced by Staphylococcus aureus. SbnA and SbnB are encoded by the staphyloferrin B biosynthetic gene cluster and are implicated in L-Dap biosynthesis. We demonstrate here that SbnA uses PLP and substrates O-phospho-L-serine and L-glutamate to produce a metabolite N-(1-amino-1-carboxyl-2-ethyl)-glutamic acid (ACEGA). SbnB is shown to use NAD+ to oxidatively hydrolyze ACEGA to yield α-ketoglutarate and L-Dap. Also, we describe crystal structures of SbnB in complex with NADH and ACEGA as well as with NAD+ and α-ketoglutarate to reveal the residues required for substrate binding, oxidation, and hydrolysis. SbnA and SbnB contribute to the iron sparing response of S. aureus that enables staphyloferrin B biosynthesis in the absence of an active tricarboxylic acid cycle.

Total synthesis of nominal (11S)- and (11R)-cyclocinamide A

The cyclocinamides possess a unique β2αβ 2α 14-membered tetrapeptide core. The initially reported biological data and intriguing structure, which was without full stereochemical identification, necessitated synthesis of both nominal (all-S) cyclocinamide A and the 11R isomer. The completed synthesis is highlighted by the use of a (cyclo)asparagine-containing dipeptide as a turn inducing fragment. Due to inconsistencies in analytical data between natural and synthetic samples, a re-evaluation of the natural product stereochemistry appears necessary.