7-Hydro-8-methylpteroylglutamyl-glutamic acid
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| Category | Others |
| Catalog number | BBF-00981 |
| CAS | 108402-49-9 |
| Molecular Weight | 586.55 |
| Molecular Formula | C25H30N8O9 |
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Description
7-Hydro-8-methylpteroylglutamyl-glutamic acid is an antifolate produced by actinomycete SK-2049. It only has the activity against Enterococcus faecium and has no effect on other bacteria and fungi. Thymidine and folate-related compounds can counteract its activity.
Specification
| Synonyms | 7-Hydro-8-methylpteroylglutamyl-glutamic acid; N-(N-(4-(((2-Amino-1,4,7,8-tetrahydro-8-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-gamma-glutamyl)-L-glutamic acid; L-Glutamic acid, N-(N-(4-(((2-amino-1,4,7,8-tetrahydro-8-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-gamma-glutamyl)- |
| IUPAC Name | (2S)-2-[[(4S)-4-[[4-[(2-amino-8-methyl-4-oxo-3,7-dihydropteridin-6-yl)methylamino]benzoyl]amino]-4-carboxybutanoyl]amino]pentanedioic acid |
| Canonical SMILES | CN1CC(=NC2=C1N=C(NC2=O)N)CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)O)C(=O)O)C(=O)O |
| InChI | InChI=1S/C25H30N8O9/c1-33-11-14(28-19-20(33)31-25(26)32-22(19)38)10-27-13-4-2-12(3-5-13)21(37)30-16(24(41)42)6-8-17(34)29-15(23(39)40)7-9-18(35)36/h2-5,15-16,27H,6-11H2,1H3,(H,29,34)(H,30,37)(H,35,36)(H,39,40)(H,41,42)(H3,26,31,32,38)/t15-,16-/m0/s1 |
| InChI Key | VNUXXWFZEBNXLN-HOTGVXAUSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | >196°C(dec.) |
| Density | 1.63 g/cm3 |
Reference Reading
1. Synthesis and Application of Constrained Amidoboronic Acids Using Amphoteric Boron-Containing Building Blocks
Harjeet S Soor, Diego B Diaz, Ka Yi Tsui, Karina Calvopiña, Marcin Bielinski, Dean J Tantillo, Christopher J Schofield, Andrei K Yudin J Org Chem. 2022 Jan 7;87(1):94-102. doi: 10.1021/acs.joc.1c02015. Epub 2021 Dec 13.
Amidoboronic acid-containing peptidomimetics are an important class of scaffolds in chemistry and drug discovery. Despite increasing interest in boron-based enzyme inhibitors, constrained amidoboronic acids have received little attention due to the limited options available for their synthesis. We describe a new methodology to prepare both α- and β-amidoboronic acids that impose restrictions on backbone angles. Lewis acid-promoted Boyer-Schmidt-Aube lactam ring expansions using an azidoalkylboronate enabled generation of constrained α-amidoboronic acid derivatives, whereas assembly of the homologous β-amidoboronic acids was achieved through a novel boronic acid-mediated lactamization process stemming from an α-boryl aldehyde. The results of quantum chemical calculations suggest carboxylate-boron coordination to be rate-limiting for small ring sizes, whereas the tetrahedral intermediate formation is rate limiting in the case of larger rings. As part of this study, an application of β-amidoboronic acid derivatives as novel VIM-2 metallo-β-lactamase inhibitors has been demonstrated.
2. Simultaneous Quantification of Organic Acids in Tamarillo ( Solanum betaceum) and Untargeted Chemotyping Using Methyl Chloroformate Derivatisation and GC-MS
Chris Pook, Tung Thanh Diep, Michelle Ji Yeon Yoo Molecules. 2022 Feb 15;27(4):1314. doi: 10.3390/molecules27041314.
Sixteen organic acids were quantified in peel and pulp of Amber, Laird's Large and Mulligan cultivars of tamarillo using GC-MS. Fourteen of these compounds had not previously been quantified in tamarillo. An untargeted metabolomics approach was used in parallel to identify and quantify 64 more metabolites relative to the internal standard, indicating abundances of glutamic acid, pro-line, aspartic acid and γ-aminobutyric acid as well as lower concentrations of several other essential fatty acids and amino acids. The main findings were that total organic acid concentration was significantly higher (p < 0.05) in pulp than in peel, with the highest concentration seen in Mulligan pulp (219.7 mg/g DW). Remarkably, after citric acid, the potent bactericide itaconic acid was the second most abundant organic acid. At least 95% of organic acids in tamarillo were one of these two acids, as well as cis-aconitic, malic and 4-toluic acids. Differences between cultivar chemotypes were as substantial as differences between tissues. These results suggest that the bitter flavour of the peel does not result from organic acids. The combination of targeted and untargeted metabolomics techniques for simultaneous qualitative and quantitative investigation of nutrients and flavours is efficient and informative.
3. Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis: Synthesis of Phenanthrenes via Phosphomolybdic Acid as a Catalyst
Yi Chen, Di Liu, Rui Wang, Li Xu, Jingyao Tan, Mao Shu, Lingfeng Tian, Yuan Jin, Xiaoke Zhang, Zhihua Lin J Org Chem. 2022 Jan 7;87(1):351-362. doi: 10.1021/acs.joc.1c02385. Epub 2021 Dec 20.
Compared with the impressive achievements of catalytic carbonyl-olefin metathesis (CCOM) mediated by Lewis acid catalysts, exploration of the CCOM through Brønsted acid-catalyzed approaches remains quite challenging. Herein, we disclose a synthetic protocol for the construction of a valuable polycycle scaffold through the CCOM with the inexpensive, nontoxic phosphomolybdic acid as a catalyst. The current annulations could realize carbonyl-olefin, carbonyl-alcohol, and acetal-alcohol in situ CCOM reactions and feature mild reaction conditions, simple manipulation, and scalability, making this strategy a promising alternative to the Lewis acid-catalyzed COM reaction.
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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 ╳
