Prolylglutamic acid
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Prolylglutamic acid

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Category
Others
Catalog number
BAT-014942
CAS number
67644-00-2
Molecular Formula
C10H16N2O5
Molecular Weight
244.24
IUPAC Name
(2S)-2-[[(2S)-pyrrolidine-2-carbonyl]amino]pentanedioic acid
Synonyms
L-Prolyl-L-glutamic acid; Pro-glu; Prolyl-Glutamate; L-Pro-L-Glu; N-L-Prolyl-L-glutamic acid
Appearance
White Powder
Purity
>99%
Sequence
H-Pro-Glu-OH
InChI
InChI=1S/C10H16N2O5/c13-8(14)4-3-7(10(16)17)12-9(15)6-2-1-5-11-6/h6-7,11H,1-5H2,(H,12,15)(H,13,14)(H,16,17)/t6-,7-/m0/s1
InChI Key
QLROSWPKSBORFJ-BQBZGAKWSA-N
Canonical SMILES
C1CC(NC1)C(=O)NC(CCC(=O)O)C(=O)O
1. Proteomic study of bioactive peptides from tempe
Badrut Tamam, Dahrul Syah, Maggy Thenawidjaja Suhartono, Wisnu Ananta Kusuma, Shinjiro Tachibana, Hanifah Nuryani Lioe J Biosci Bioeng. 2019 Aug;128(2):241-248. doi: 10.1016/j.jbiosc.2019.01.019. Epub 2019 Mar 29.
Tempe is a traditional Indonesian fermented soybean mostly produced in small industries and sold locally throughout the country. Studies on the bioactive peptides in tempe are rare. Here, we studied bioactive peptides in samples from three tempe producers with different degrees of sanitation. The peptide sub-fractions of tempe from each producer were collected following water extraction, ultrafiltration (<3 kDa), gel filtration chromatography, and reversed phase-high performance liquid chromatography (RP-HPLC) separation followed by liquid chromatography-mass spectrometry (LC-MS). The MS spectra were then predicted using FindPept tools, and their biofunctionalities were confirmed with BIOPEP databases. There were few similar peptides found in tempe from the three producers. Peptides Val-His and Ala-Leu-Glu-Pro were found in tempe from all producers. Producers having a good sanitation level had more bioactive peptides than those with moderate or poor sanitation levels (58%, 43% and 35%, from good to poor sanitation). This work showed that the tempe from the three producers had antihypertensive, antidiabetic, antioxidative and antitumor peptides.
2. New Nanocarrier System for Liposomes Coated with Lactobacillus acidophilus S-Layer Protein to Improve Leu-Gln-Pro-Glu Absorption through the Intestinal Epithelium
Xiaoxiao Jiang, Daodong Pan, Mingxuan Tao, Tao Zhang, Xiaoqun Zeng, Zhen Wu, Yuxing Guo J Agric Food Chem. 2021 Jul 14;69(27):7593-7602. doi: 10.1021/acs.jafc.1c01498. Epub 2021 Jun 30.
The present study describes the development of a novel liposome nanocarrier system. The liposome was coated with Lactobacillus acidophilus CICC 6074 S-layer protein (SLP) to improve the intestinal absorption of the cholesterol-lowering peptide Leu-Gln-Pro-Glu (LQPE). The SLP-coated liposomes were prepared and characterized with morphology, particle size, zeta potential, membrane stability, Fourier transform infrared spectroscopy, and dual-channel surface plasma resonance. The results showed that SLP could successfully self-assemble on liposomes. Then, LQPE liposomes and SLP-coated LQPE liposomes (SLP-L-LQPE) were prepared. SLP-L-LQPE not only showed better sustained release properties and gastrointestinal tolerance in vitro but also increased the retention time in mice intestine. Transepithelial transport experiment indicates that the transshipment of LQPE increased significantly after being embedded by liposomes and coated with SLP. The research provides a theoretical basis for the study of SLP-coated liposomes and a potential drug delivery system for improving the intestinal absorption of peptides.
3. Isolation and identification of the umami peptides from shiitake mushroom by consecutive chromatography and LC-Q-TOF-MS
Yan Kong, Li-Li Zhang, Jing Zhao, Yu-Yu Zhang, Bao-Guo Sun, Hai-Tao Chen Food Res Int. 2019 Jul;121:463-470. doi: 10.1016/j.foodres.2018.11.060. Epub 2018 Nov 29.
Umami is critical to the taste of shiitake mushroom. To isolate and identify umami peptides, fractions from hydrolyzed dried shiitake mushroom were separated by ultrafiltration, gel filtration chromatography (GFC), and reversed-phase high-performance liquid chromatography (RP-HPLC). Separations were combined with sensory evaluations (grading and taste dilution analysis) and analysis of electronic tongue, which were used to identify the most umami component in shiitake mushroom. Low-molecular-weight fractions (MW < 3 kDa) have the strongest flavor in the shiitake mushroom hydrolysate. In the 3 subfractions separated from low-molecular-weight fractions (MW < 3 kDa) by GFC, the second subfraction (F2) was selected for RP-HPLC analysis. The first peak (G1) in RP-HPLC was identified by LC-Q-TOF-MS, and 2 tripeptides and 3 dipeptides were identified. The amino acid sequence of these peptides were Gly-Cys-Gly, Glu-Pro-Glu, Cys-Met, Val-Phe, and Gly-Glu.
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