Glutamyl-glutamine
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-05111 |
| CAS | 26848-14-6 |
| Molecular Weight | 275.26 |
| Molecular Formula | C10H17N3O6 |
Online Inquiry
Specification
| Synonyms | L-Glutamyl-L-Glutamine; Glu-Gln |
| Sequence | H-Glu-Gln-OH |
| IUPAC Name | (4S)-4-amino-5-[[(1S)-4-amino-1-carboxy-4-oxobutyl]amino]-5-oxopentanoic acid |
| Canonical SMILES | C(CC(=O)O)C(C(=O)NC(CCC(=O)N)C(=O)O)N |
| InChI | InChI=1S/C10H17N3O6/c11-5(1-4-8(15)16)9(17)13-6(10(18)19)2-3-7(12)14/h5-6H,1-4,11H2,(H2,12,14)(H,13,17)(H,15,16)(H,18,19)/t5-,6-/m0/s1 |
| InChI Key | MGHKSHCBDXNTHX-WDSKDSINSA-N |
Properties
| Boiling Point | 757.1±60.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. A Novel Gd-DTPA-conjugated Poly(L-γ-glutamyl-glutamine)-paclitaxel Polymeric Delivery System for Tumor Theranostics
Lipeng Gao, Jinge Zhou, Jing Yu, Qilong Li, Xueying Liu, Lei Sun, Ting Peng, Jing Wang, Jianzhong Zhu, Jihong Sun, Weiyue Lu, Lei Yu, Zhiqiang Yan, Yiting Wang Sci Rep. 2017 Jun 19;7(1):3799. doi: 10.1038/s41598-017-03633-9.
The conventional chemotherapeutics could not be traced in vivo and provide timely feedback on the clinical effectiveness of drugs. In this study, poly(L-γ-glutamyl-glutamine)-paclitaxel (PGG-PTX), as a model polymer, was chemically conjugated with Gd-DTPA (Gd-diethylenetriaminepentaacetic acid), a T1-contrast agent of MRI, to prepare a Gd-DTPA-conjugated PGG-PTX (PGG-PTX-DTPA-Gd) delivery system used for tumor theranostics. PGG-PTX-DTPA-Gd can be self-assembled to NPs in water with a z-average hydrodynamic diameter about 35.9 nm. The 3 T MRI results confirmed that the relaxivity of PGG-PTX-DTPA-Gd NPs (r1 = 18.98 mM-1S-1) was increased nearly 4.9 times compared with that of free Gd-DTPA (r1 = 3.87 mM-1S-1). The in vivo fluorescence imaging results showed that PGG-PTX-DTPA-Gd NPs could be accumulated in the tumor tissue of NCI-H460 lung cancer animal model by EPR effect, which was similar to PGG-PTX NPs. The MRI results showed that compared with free Gd-DTPA, PGG-PTX-DTPA-Gd NPs showed significantly enhanced and prolonged signal intensity in tumor tissue, which should be attributed to the increased relaxivity and tumor accumulation. PGG-PTX-DTPA-Gd NPs also showed effective antitumor effect in vivo. These results indicated that PGG-PTX-DTPA-Gd NPs are an effective delivery system for tumor theranostics, and should have a potential value in personalized treatment of tumor.
2. From Batch to Continuous Flow Bioprocessing: Use of an Immobilized γ-Glutamyl Transferase from B. subtilis for the Synthesis of Biologically Active Peptide Derivatives
Marina S Robescu, Francesca Annunziata, Valeria Somma, Cinzia Calvio, Carlo F Morelli, Giovanna Speranza, Lucia Tamborini, Daniela Ubiali, Andrea Pinto, Teodora Bavaro J Agric Food Chem. 2022 Oct 26;70(42):13692-13699. doi: 10.1021/acs.jafc.2c03702. Epub 2022 Sep 23.
γ-Glutamyl-peptides are frequently endowed with biological activities. In this work, "kokumi peptides" such as γ-glutamyl-methionine (1) and γ-glutamyl-(S)-allyl-cysteine (2), as well as the neuroprotective γ-glutamyl-taurine (3) and the antioxidant ophthalmic acid (4), were synthesized through an enzymatic transpeptidation reaction catalyzed by the γ-glutamyl transferase from Bacillus subtilis (BsGGT) using glutamine as the γ-glutamyl donor. BsGGT was covalently immobilized on glyoxyl-agarose resulting in high protein immobilization yield and activity recovery (>95%). Compounds 1-4 were obtained in moderate yields (19-40%, 5-10 g/L) with a variable purity depending on the presence of the main byproduct (γ-glutamyl-glutamine, 0-16%). To achieve process intensification and better control of side reactions, the synthesis of 2 was moved from batch to continuous flow. The specific productivity was 1.5 times higher than that in batch synthesis (13.7 μmol/min*g), but it was not accompanied by a paralleled improvement of the impurity profile.
3. Fearful dogs have increased plasma glutamine and γ-glutamyl glutamine
Jenni Puurunen, Katriina Tiira, Katariina Vapalahti, Marko Lehtonen, Kati Hanhineva, Hannes Lohi Sci Rep. 2018 Oct 29;8(1):15976. doi: 10.1038/s41598-018-34321-x.
Anxiety-related disorders, including fearfulness are common and leading welfare problems among the worldwide dog population. The etiology of anxieties is complex and affected by genetic and environmental factors. Thus, there is a need for more comprehensive approaches, such as metabolomics, to understand the causes of anxiety and to identify anxiety-related biomarkers for more efficient diagnostic and treatment options. To study metabolic alterations related to canine fearfulness, a non-targeted plasma metabolite profiling was performed in a cohort of 20 fearful and 21 non-fearful dogs. The results showed that nine metabolic features were significantly associated with fearfulness. The most prominent change included increased plasma glutamine and γ-glutamyl glutamine (γ-Glu Gln) in fearful dogs across breeds. Alterations in glutamine metabolism have previously been associated with several psychiatric disorders, indicating the relevance of this finding also in dogs. In addition, we describe a novel breed-specific association between renal biomarker symmetric dimethylarginine (SDMA) and canine fearfulness. These observed metabolic alterations may result from high levels of prolonged psychological stress in fearful dogs.
Recommended Products
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
