L-Allylglycine

Base Information

• Chemical Name: L-Allylglycine
• CAS No.: 16338-48-0
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.132
• Hs Code.: 29224999
• Mol file: 16338-48-0.mol

Synonyms:(2S)-2-aminopent-4-enoic acid;4-Pentenoic acid, 2-amino-, (S)-;(-)-Allylglycine;L-Allylglycine;(S)-2-Amino-4-pentenoic acid;L-alpha-Allyl-Gly;

Chemical Property of L-Allylglycine

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 0.0226mmHg at 25°C
• Melting Point: 253-255 °C
• Refractive Index: 1.484
• Boiling Point: 231 °C at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 93.5 °C
• PSA: 63.32000
• Density: 1.098 g/cm³
• LogP: 0.67470
• Storage Temp.: 2-8°C
• Solubility.: H2O: 100 mg/mL
• Water Solubility.: soluble

Purity/Quality:

97% ^*data from raw suppliers

L-Allylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: L-Allylglycine is a glutamic acid decarboxylase inhibitor.

Technology Process of L-Allylglycine

There total 28 articles about L-Allylglycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (100516-55-0) → D-allylglycine (54594-06-8) + L-allylglycine (16338-48-0)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; ethanol; for 1h; Yields of byproduct given;

DOI:10.1021/ja00213a031

Reference yield:

allyl bromide (106-95-6) + glycine (56-40-6,18875-39-3,25718-94-9) → D-allylglycine (54594-06-8) + L-allylglycine (16338-48-0)

Guidance literature:

glycine; With pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide; sodium methylate; nickel(II) nitrate; In methanol; for 0.333333h; Heating;

allyl bromide; With sodium hydroxide; (R)-2-amino-2'-hydroxy-1,1'-binaphthyl; In dichloromethane; at 20 ℃; for 0.5h;

With hydrogenchloride; In methanol; water; Heating;

DOI:10.1002/1521-3773(20010518)40:10<1948::AID-ANIE1948>3.0.CO;2-O

Reference yield:

allyl iodid (556-56-9) + glycine (56-40-6,18875-39-3,25718-94-9) → D-allylglycine (54594-06-8) + L-allylglycine (16338-48-0)

Guidance literature:

glycine; With pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide; sodium methylate; nickel(II) nitrate; In methanol; for 0.333333h; Heating;

allyl iodid; With sodium hydroxide; (R)-2-amino-2'-hydroxy-1,1'-binaphthyl; In dichloromethane; at 20 ℃; for 0.0666667h;

With hydrogenchloride; In methanol; water; Heating;

DOI:10.1002/1521-3773(20010518)40:10<1948::AID-ANIE1948>3.0.CO;2-O

upstream raw materials:

α-allylglycine amide

benzaldehyde

2-Amino-N-methoxy-4-pentenamide

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Downstream raw materials:

methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

Boc-Alg-D-Val-ONb

L-phenoxyacetyl allylglycine

Refernces

A convenient and efficient synthesis of (S)-lysine and (S)-arginine homologues via olefin cross-metathesis

10.1016/j.tet.2005.05.021

The research focuses on the efficient synthesis of (S)-homolysine and (S)-bishomoarginine, which are analogues of the cationic amino acids lysine and arginine, respectively. These homologues are valuable in drug discovery, particularly in the development of peptidic enzyme inhibitors and for probing enzyme active sites. The synthesis strategy avoids the use of chiral templates by incorporating commercially available (S)-allylglycine and utilizes olefin cross-metathesis for chain elongation. The synthesis of (S)-homolysine involves five steps with an overall yield of 55%, which is an improvement over previous methods. (S)-Bishomoarginine is prepared in six steps with a 57% overall yield. Key reactants include bromobutene, di-tert-butyliminodicarboxylate, cesium carbonate, and Grubbs’ ruthenium catalyst, among others. The synthesis involves protection and deprotection steps, cross-metathesis reactions, and hydrogenation. Analyses used to confirm the structure and purity of the compounds include NMR spectroscopy, specific rotation measurements, and chiral GC analysis.