504-91-6

Basic information

• Product Name: 2-amino-4-(2-aminoethoxy)butanoic acid
• Synonyms: 2-amino-4-(2-aminoethoxy)butanoic acid;2,6-Diamino-5-hydroxyhexanoic acid
• CAS NO: 504-91-6
• Molecular Formula: C₆H₁₄N₂O₃
• Molecular Weight: 0
• Mol File: 504-91-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 288.88°C (rough estimate)
• Flash Point: 205.5°C
• Appearance: /
• Density: 1.2266 (rough estimate)
• Vapor Pressure: 4.47E-06mmHg at 25°C
• Refractive Index: 1.4650 (estimate)
• CAS DataBase Reference: 2-amino-4-(2-aminoethoxy)butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-4-(2-aminoethoxy)butanoic acid(504-91-6)
• EPA Substance Registry System: 2-amino-4-(2-aminoethoxy)butanoic acid(504-91-6)

Safety Data

• Hazardous Substances Data: 504-91-6(Hazardous Substances Data)

Usage

Classification

Amino acid derivative

Potential applications

Treatment of metabolic disorders, precursor for synthesis of pharmaceutical compounds

Structure

Butanoic acid core with amino group at 2-position and aminoethoxy group at 4-position

InChI:InChI=1/C6H14N2O3/c7-2-4-11-3-1-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)

Upstream product

• 220244-01-9 (2S,5R)-(-)-tert-butyl-6-amino-2-[(tert-butoxycarbonyl)amino]-5-hydroxyhexanoate 
• 321307-56-6 (R)-5-((S)-3-Amino-3-carboxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 309928-96-9 (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-hydroxyhexanoic acid 
• 56-87-1 L-lysine 
• 15366-19-5 methyl (S)-2-benzyloxycarbonylamino-6-diazo-5-oxohexanoate 
• 58456-27-2 (S)-3-(benzyloxycarbonyl)-4-(4-diazo-3-oxobutyl)-5-oxazolidinone 
• 309928-91-4 methyl (2S)-2-benzyloxycarbonylamino-6-bromo-5-oxohexanoate 
• 309928-94-7 (2S,5R)-5-azidomethyl-2-benzyloxycarbonylamino-δ-valerolactone 
• 309928-92-5 methyl (S)-6-azido-2-benzyloxycarbonylamino-5-oxohexanoate 
• 24277-39-2 N-tert-butoxycarbonyl glutamic acid tert-butyl ester 
• 208520-00-7 (S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester 
• 220243-88-9 (2S)-tert-butyl 6-bromo-2-[(tert-butoxycarbonyl)amino]-5-hydroxyhexanoate 
• 220243-87-8 (S)-6-bromo-2-tert-butoxycarbonylamino-5-oxohexanoic acid tert-butyl ester 
• 220244-00-8 1-tert-butyl (2S,5R)-6-azido-2-[N-(tert-butoxycarbonyl)-amino]-5-hydroxyhexanoate 

Downstream Products

• 107621-96-5 DL-threo-N²,N⁶-bis-(2,4-dinitro-phenyl)-5-hydroxy-lysine lactone 
• 95020-49-8 DL-threo-N²,N⁶-bis-(2,4-dinitro-phenyl)-5-hydroxy-lysine 
• 79432-14-7 (2S,5R)-2-amino-6-[(benzyloxycarbonyl)amino]-5-hydroxyhexanoic acid 
• 270089-67-3 (5R)-N^α-(fluoren-9-ylmethoxycarbonyl)-N^ε-benzyloxycarbonyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-5-hydroxy-L-lysine 
• 851857-30-2 (2S,5R)-2-Amino-6-benzyloxycarbonylamino-5-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid 
• 104947-69-5 bengamide B 
• 334905-26-9 (3S,6S)-3-(tert-butyloxycarbonyl)aminohexahydro-6-(4-nitrophenylcarbonyl)oxy-2H-azepin-2-one 
• 334905-27-0 (3S,6S)-1-methyl-3-(tert-butyloxycarbonyl)aminohexahydro-6-(4-nitrophenylcarbonyl)oxy-2H-azepin-2-one 
• 50439-45-7 (2S,5R)-5-hydroxy-2-piperidinecarboxylic acid 
• 63088-78-8 (2S,5R)-5-hydroxypiperidine-2-carboxylic acid 
• 2906-39-0 Δ¹-pyrroline-5-carboxylate 

Relevant articles and documents

Facile synthesis of 5-hydroxy-l-lysine from d-galactose as a chiral-precursor

A concise synthesis of (2S,5R) and (2S,5S)-5-hydroxy-lysine was achieved by utilizing d-galactose as a chiral-precursor with stereo retention. This synthetic strategy showcased the potential of utilizing carbohydrates as starting materials to prepare amino acids. Using the diazido intermediate, the derived β-d-galactopyranosyl and α-d-glucopyranosyl-(1→2)- β-d-galactosyl moieties were synthesized. This journal is the Partner Organisations 2014.

The 2-Oxoglutarate-Dependent Oxygenase JMJD6 Catalyses Oxidation of Lysine Residues to give 5S-Hydroxylysine Residues

Amino acid analyses reveal that JMJD6-catalysed hydroxylation of RNA-splicing regulatory protein fragments occurs to give hydroxylysine products with 5S stereochemistry. This contrasts with collagen lysyl hydroxylases, which give 5R-hydroxylated products. The work suggests that more than one subfamily of lysyl hydroxylases has evolved and illustrates the importance of stereochemical assignments in proteomic analyses.

Stereoselective synthesis of (2R,5R)- and (2S,5R)-5-hydroxylysine

A stereoselective synthesis of (2S,5R)-5-hydroxylysine (1) and (2R,5R)-5-hydroxylysine (17), based on a concept involving Williams glycine template methodology and (R)-hydroxynitrile lyase for the introduction of chirality at the α-position and the side-chain, respectively, is described. This strategy offers an expeditious route towards orthogonally protected 5-hydroxylysines.