(2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate
• CAS No.: 71-00-1
• Molecular Formula: C6H9N3O2
• Molecular Weight: 155.156
• Hs Code.: HISTIDINE PRODUCT IDENTIFICATION
• Mol file: 71-00-1.mol

Synonyms:(2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate;[3H]histidine;[3H]-histidine;L-histidine zwitterion;2q2c;D07UTZ;CHEBI:57595;alpha-amino-4-imidazoleproprionic acid;(2S)-2-ammonio-3-(1H-imidazol-4-yl)propanoate;(2S)-2-ammonio-3-(1H-imidazol-5-yl)propanoate;A837047;(2S)-2-azaniumyl-3-(1H-imidazol-4-yl)propanoate

Chemical Property of (2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 282 °C (dec.)(lit.)
• Refractive Index: 13 ° (C=11, 6mol/L HCl)
• Boiling Point: 458.9 °C at 760 mmHg
• PKA: 1.91±0.10(Predicted)
• Flash Point: 231.3 °C
• PSA: 92.00000
• Density: 1.423 g/cm³
• LogP: 0.06440
• Water Solubility.: 41.6 g/L (25℃)
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 155.069476538
• Heavy Atom Count: 11
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(NC=N1)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=C(NC=N1)C[C@@H](C(=O)[O-])[NH3+]
• Chemical Description: Histidine is an alpha-amino acid containing an isopyrazole ring. It is a constituent amino acid of body proteins and is found in some functional proteins such as histones and hemoglobin.; Histidine residues and isopyrazole rings are components of enzyme proteins and functional parts of certain proteins. It's structure includes an α-amino group, a carboxylic acid group, and an imidazole side chain.Under physiological conditions, the amino group is protonated, and the carboxylic group is deprotonated.
• Physiological Functions: Histidine is a natural chelating agent and is involved in the structure and function of many enzymes.; Free histidine, small peptides containing histidine, and histamine generated from histidine decarboxylation all have specific physiological functions.; It plays a role in metabolism and affects various metabolic processes in the body.
• Molecular Interactions: The versatility of histidine in molecular interactions arises from its unique molecular structure. Histidine's imidazole side chain can engage in various molecular interactions, including cation-π interaction, π-π stacking interaction, hydrogen-π interaction, coordinate bond interaction, and hydrogen bond interaction. These interactions contribute to histidine's role in protein structure, enzymatic function, and other physiological processes.
• Nutritional and Therapeutic Uses: Histidine is considered an essential amino acid for young children but non-essential for adults. It has been used as a nutritional supplement in various conditions such as rheumatoid arthritis, anaemia in chronic renal failure, fatigue during exercise, ageing-related disorders, metabolic syndrome, atopic dermatitis, ulcers, inflammatory bowel diseases, ocular diseases, and neurological disorders.

Technology Process of (2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate

There total 111 articles about (2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate 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:

Hizikia fusiformis lectine → L-alanin (56-41-7,25191-17-7,18875-37-1) + L-Cysteine (52-90-4) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + L-methionine (63-68-3,26062-47-5,58576-49-1) + L-lysine (56-87-1,3506-25-0) + L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + L-arginine (74-79-3,25212-18-4) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) + L-histidine (71-00-1)

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1016/j.foodchem.2016.01.061

Reference yield:

type I collagen from Bester sturgeon scales → L-alanin (56-41-7,25191-17-7,18875-37-1) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + L-serin (56-45-1,83245-15-2) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + L-methionine (63-68-3,26062-47-5,58576-49-1) + L-lysine (56-87-1,3506-25-0) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + (5R)-5-hydroxy-L-lysine (504-91-6,1190-94-9,3506-26-1,6000-08-4,18899-29-1,18899-30-4,18899-31-5,52153-41-0,78088-29-6,28902-93-4) + L-arginine (74-79-3,25212-18-4) + S,S-cystine (349-46-2) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) + glycine (56-40-6,18875-39-3,25718-94-9) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) + 4R-4-hydroxyproline (51-35-4,30724-02-8) + L-histidine (71-00-1)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 24h;

DOI:10.1016/j.foodchem.2014.03.075

Reference yield:

type I collagen from Bester sturgeon skin → L-alanin (56-41-7,25191-17-7,18875-37-1) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + L-serin (56-45-1,83245-15-2) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + L-methionine (63-68-3,26062-47-5,58576-49-1) + L-lysine (56-87-1,3506-25-0) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + (5R)-5-hydroxy-L-lysine (504-91-6,1190-94-9,3506-26-1,6000-08-4,18899-29-1,18899-30-4,18899-31-5,52153-41-0,78088-29-6,28902-93-4) + L-arginine (74-79-3,25212-18-4) + S,S-cystine (349-46-2) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) + glycine (56-40-6,18875-39-3,25718-94-9) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) + 4R-4-hydroxyproline (51-35-4,30724-02-8) + L-histidine (71-00-1)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 24h;

DOI:10.1016/j.foodchem.2014.03.075

upstream raw materials:

ammonia

2-chloro-3-(1H-imidazol-4-yl)propanoic acid

sulfuric acid

Carnosine

Downstream raw materials:

N^α-(1-benzyloxycarbonyl-L-prolyl)-L-histidine

N^α-formyl-histidine

1,N^α-dipicryl-histidine

4-cyanomethylimidazole

Refernces

• 1、 Wang, Jun,Liu, Kaiying,Sun, Guangming,Bai, Jiling,Wang, Li. "High-throughput screening for the asymmetric transformation reaction of L-histidine to D-histidine by capillary array electrophoresis". . p. 901 - 904. Retrieved 2006.
• 2、 Bauer, Carsten,Liao, Cangsong,Peng, Jiaming,Seebeck, Florian P.. "Fluorinated S-Adenosylmethionine as a Reagent for Enzyme-Catalyzed Fluoromethylation". . p. 27178 - 27183. Retrieved 2021/11/16.
• 3、 Yin, Dong-Ya,Pan, Jiang,Zhu, Jie,Liu, You-Yan,Xu, Jian-He. "A green-by-design bioprocess for l-carnosine production integrating enzymatic synthesis with membrane separation". . p. 5971 - 5978. Retrieved 2019/11/14.