2-N-Fmoc-amino-3-(4-N-Boc-piperidinyl)propionic acid
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2-N-Fmoc-amino-3-(4-N-Boc-piperidinyl)propionic acid

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Category
Fmoc-Amino Acids
Catalog number
BAT-014337
CAS number
313052-02-7
Molecular Formula
C28H34N2O6
Molecular Weight
494.60
2-N-Fmoc-amino-3-(4-N-Boc-piperidinyl)propionic acid
IUPAC Name
2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propanoic acid
Synonyms
N-Fmoc-DL-amino-3-(N-Boc-4-piperidinyl)propionic acid
Appearance
White to Off-white Solid
Purity
97.0%
Storage
Store at 2-8°C
InChI
InChI=1S/C28H34N2O6/c1-28(2,3)36-27(34)30-14-12-18(13-15-30)16-24(25(31)32)29-26(33)35-17-23-21-10-6-4-8-19(21)20-9-5-7-11-22(20)23/h4-11,18,23-24H,12-17H2,1-3H3,(H,29,33)(H,31,32)
InChI Key
JVDSTYGNXVJVKL-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CCC(CC1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
1. The Mechanism Underlying the Influence of Indole-3-Propionic Acid: A Relevance to Metabolic Disorders
Binbin Zhang, Minjie Jiang, Jianan Zhao, Yu Song, Weidong Du, Junping Shi Front Endocrinol (Lausanne). 2022 Mar 18;13:841703. doi: 10.3389/fendo.2022.841703. eCollection 2022.
The increasing prevalence of metabolic syndrome has become a serious public health problem. Certain bacteria-derived metabolites play a key role in maintaining human health by regulating the host metabolism. Recent evidence shows that indole-3-propionic acid content can be used to predict the occurrence and development of metabolic diseases. Supplementing indole-3-propionic acid can effectively improve metabolic disorders and is considered a promising metabolite. Therefore, this article systematically reviews the latest research on indole-3-propionic acid and elaborates its source of metabolism and its association with metabolic diseases. Indole-3-propionic acid can improve blood glucose and increase insulin sensitivity, inhibit liver lipid synthesis and inflammatory factors, correct intestinal microbial disorders, maintain the intestinal barrier, and suppress the intestinal immune response. The study of the mechanism of the metabolic benefits of indole-3-propionic acid is expected to be a potential compound for treating metabolic syndrome.
2. Propionic Acid Shapes the Multiple Sclerosis Disease Course by an Immunomodulatory Mechanism
Alexander Duscha, et al. Cell. 2020 Mar 19;180(6):1067-1080.e16. doi: 10.1016/j.cell.2020.02.035. Epub 2020 Mar 10.
Short-chain fatty acids are processed from indigestible dietary fibers by gut bacteria and have immunomodulatory properties. Here, we investigate propionic acid (PA) in multiple sclerosis (MS), an autoimmune and neurodegenerative disease. Serum and feces of subjects with MS exhibited significantly reduced PA amounts compared with controls, particularly after the first relapse. In a proof-of-concept study, we supplemented PA to therapy-naive MS patients and as an add-on to MS immunotherapy. After 2 weeks of PA intake, we observed a significant and sustained increase of functionally competent regulatory T (Treg) cells, whereas Th1 and Th17 cells decreased significantly. Post-hoc analyses revealed a reduced annual relapse rate, disability stabilization, and reduced brain atrophy after 3 years of PA intake. Functional microbiome analysis revealed increased expression of Treg-cell-inducing genes in the intestine after PA intake. Furthermore, PA normalized Treg cell mitochondrial function and morphology in MS. Our findings suggest that PA can serve as a potent immunomodulatory supplement to MS drugs.
3. Propionic acid-rich fermentation (PARF) production from organic wastes: A review
Yuexi Chen, Xuemeng Zhang, Yinguang Chen Bioresour Technol. 2021 Nov;339:125569. doi: 10.1016/j.biortech.2021.125569. Epub 2021 Jul 17.
Nowadays, increasing attention has been drawn to biological valorization of organic wastes. Wherein, propionic acid-rich fermentation (PARF) has become a focal point of research. The objective of this review is to make a thorough investigation on the potential of PARF production and give future outlook. By discussing the key factors affecting PARF including substrate types, pH, temperature, retention time, etc., and various improving methods to enhance PARF including different pretreatments, inoculation optimization and immobilization, a comprehensive summary on how to achieve PARF from organic waste is presented. Then, current application of PARF liquid is concluded, which is found to play an essential role in the efficient denitrification and phosphorus removal of wastewater and preparation of microbial lipids. Finally, the environmental performance of PARF production is reviewed through life cycle assessment studies, and environmentally sensitive sectors are summarized for process optimization, providing a reference for waste management in low carbon scenarios.
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