4-Amino-DL-phenylalanine
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4-Amino-DL-phenylalanine

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Category
DL-Amino Acids
Catalog number
BAT-007851
CAS number
2922-41-0
Molecular Formula
C9H12N2O2
Molecular Weight
180.20
4-Amino-DL-phenylalanine
IUPAC Name
2-amino-3-(4-aminophenyl)propanoic acid
Synonyms
DL-Phe(4-NH2)-OH; p-Amino-DL-phenylalanine; 2-Amino-3-(4-aminophenyl)propanoic acid; 4-Amino-dl-phenylalanine; H-DL-Phe(4-NH2)-OH; p-Amino-dl-phenylalanine; 4-Aminophenylalanine; H-p-Amino-Phe-OH HCl; Phenylalanine, 4-amino-; p-AMINOPHENYL ALANINE; H-P-AMINO-DL-PHE-OH HYDRATE; para-Aminophenylalanine; L-2-Amino-3-(4-aminophenyl)propanoic acid; Dl-(4-Amino)-Phenylalanine; p-Amino-D-phenylalanine acid; DL-4-NH2-Phe-OH
Appearance
White to off-white solid
Purity
≥ 97% (HPLC)
Density
1.289 g/cm3
Melting Point
255-258 °C (dec.)
Boiling Point
383.5 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H12N2O2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,10-11H2,(H,12,13)
InChI Key
CMUHFUGDYMFHEI-UHFFFAOYSA-N
Canonical SMILES
C1=CC(=CC=C1CC(C(=O)O)N)N
1. Injectable chitin hydrogels with self-healing property and biodegradability as stem cell carriers
Xuefeng Yang, Hongye Yang, Xueyu Jiang, Boguang Yang, Kunkun Zhu, Nathanael Chun-Him Lai, Cui Huang, Chunyu Chang, Liming Bian, Lina Zhang Carbohydr Polym. 2021 Mar 15;256:117574. doi: 10.1016/j.carbpol.2020.117574. Epub 2020 Dec 30.
To meet the demands of various therapeutic tasks, injectable hydrogels with tunable mechanical properties and degradability are highly desired. Herein, we developed an injectable chitin hydrogel system with well-manipulated mechanical properties and degradability through dynamic acylhydrazone crosslinking catalyzed by 4-amino-DL-phenylalanine (Phe-NH2). The mechanical properties and degradability of the hydrogels could be easily adjusted by varying the solid content, while their gelation time could be maintained at a constant level (~130 s) by altering Phe-NH2 content, thereby ensuring the good injectability of hydrogels. Moreover, the chitin hydrogels showed excellent self-healing capacity with a healing efficiency up to 95 %. Owing to their superior biocompatibility and biodegradability, the chitin hydrogels could support the proliferation and multi-potent differentiations of rat bone marrow-derived stem cells, serving as a beneficial 3D scaffold for stem cell encapsulation and delivery. This work provides a promising injectable delivery vehicle of therapeutic drugs or cells for tissue regenerative medicine.
2. Conductive and self-healing hydrogel for flexible electrochemiluminescence sensor
Xuejiao Liu, Yang Bai, Xiaoxiao Zhao, Jun Chen, Xu Chen, Wensheng Yang Mikrochim Acta. 2023 Mar 9;190(4):123. doi: 10.1007/s00604-023-05706-1.
A flexible electrochemiluminescence (ECL) hydrogel sensor exhibiting good self-healing was constructed. A transparent self-healing oxidized sodium alginate/hydrazide polyethylene glycol (OSA/PEG-DH) hydrogel was prepared by crosslinking dynamic covalent acylhydrazone bond. The introduction of 4-amino-DL-phenylalanine, a catalyst with good biocompatibility, allows rapid gelation and self-healing of hydrogel under mild conditions. Using the hydrogel as the sensing substrate, the ionic liquid (IL) 2-hydroxy-N,N,N-trimethylethanaminium chloride and the luminescent reagent N-(aminobutyl)-N-(ethylisoluminol) (ABEI) were simultaneously immobilized in the OSA/PEG-DH hydrogel to obtain the ABEI/IL/OSA/PEG-DH hydrogel. The ABEI/IL/OSA/PEG-DH hydrogel can be directly used as a semi-solid electrolyte for constructing a flexible ECL hydrogel sensor for the detection of H2O2, which acted as a coreactant of ABEI. The prepared flexible ECL sensor showed good self-healing performance, can restore ECL signal intensity within 20 min after physical damage, and showed high accuracy in the analysis of complex serum samples. This research shed new light on the development of flexible ECL sensor for bioanalytical applications.
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