1-Pyrrolidineacetic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-α-(1-methylethyl)-2-oxo-, (αS,3R)-
N-FMOC-FREIDINGER'S LACTAM
CAS: 957507-85-6
Molecular Formula: C24H26N2O5
1-Pyrrolidineacetic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-α-(1-methylethyl)-2-oxo-, (αS,3R)- - Names and Identifiers
1-Pyrrolidineacetic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-α-(1-methylethyl)-2-oxo-, (αS,3R)- - Physico-chemical Properties
| Molecular Formula | C24H26N2O5 |
| Molar Mass | 422.47 |
| Storage Condition | 2-8°C |
1-Pyrrolidineacetic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-α-(1-methylethyl)-2-oxo-, (αS,3R)- - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
1-Pyrrolidineacetic acid, 3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-α-(1-methylethyl)-2-oxo-, (αS,3R)- - References
| Introduction | Lactam is a common cyclic structure in organic compounds, and the ring formed in the molecule has a R1-CONH-R2 structure. The ring formed by lactam is generally a four-to seven-membered ring. The lactam ring is essential to maintain the antibacterial activity of some compounds. The common β-lactam antibiotics in daily life are typical representatives. The function of these antibiotics lies in the β-lactam ring structure of the compound. |
| β-lactam drug | From the discovery of penicillin by British bacteriologist Fleming while cultivating bacteria in 1929, to the successful mass production of penicillin during the Second World War, tens of thousands of injured and infected soldiers were saved. Antibiotics have become inseparable from the health of all mankind and affect the development of the entire human society. β-lactam antibiotics are the most commercialized antibiotics on the market. As early as 2010, β-lactam antibiotics accounted for about 53% of the global antibiotic market, with an amount of US $42 billion [2]. It can be said that to a certain extent, β-lactam antibiotics affect the development of human society. β-lactam antibiotics refer to the general term for antibiotics that contain β-lactam rings in their chemical structure [3]. Dating back to around 1940, penicillin was the first β-lactam antibiotic to be used clinically [4]. Due to the emergence of penicillinase, cephalosporin antibiotics that are stable to penicillinase were developed after 1950 [5], and 3 other subtypes were developed in the following decades. In the 1980s, carbapenems represented by imipenem had the advantages of broad-spectrum antibacterial activity and effective resistance to β-lactamases at that time, and subsequently developed meropenem and ertapenem, which were more stable in chemical structure. And Dolipenem, etc. [6]. Monocyclic β-lactam antibiotics were developed in the 1980s, and their representatives are aztreonam and carulmonam [7]. As shown in Table 1, we summarize the major categories of β-lactam drugs according to the time sequence of their listing. We can find that the second half of the 20th century is the golden age of the development of β-lactam drugs, and a large number of new drugs and Compound preparations continue to emerge. |
| structure and bactericidal principle | regarding the bactericidal principle of β-lactam drugs, there is an internationally recognized theory that β-lactam antibiotics inhibit the enzymes involved in cell wall synthesis, namely penicillin binding proteins (penicillin bindingproteins, PBPs), causing cell wall damage and causing bacterial lysis and death [1]. β-lactam drugs can inhibit PBPs, which is mainly caused by the structural characteristics of β-lactam antibiotics. As shown in Figure 1, β-lactam antibiotics have a common ring structure, which has a striking structural similarity with the substrate of PBPs-D-alanine-D-alanine [3]. As early as 1970, three RockefellerUniversity scientists discovered that by inhibiting a pathway that has nothing to do with the PBPs pathway, Streptococcus pneumoniae, which was originally sensitive to penicillin, can be resistant to penicillin, which suggests that we may have other pathways for penicillin sterilization. It was later discovered that the way penicillin kills bacteria depends on an enzyme that can degrade cell wall peptidoglycan, which is autolysin [8]. Recent studies have given detailed answers to autolysin's precise regulation of peptidoglycan degradation and how penicillin makes this process out of control: penicillin reduces its expression by affecting Tacl, an enzyme that regulates autolysin [9], thereby causing autolysin to transfer from the cell membrane to the cell wall, and finally causing peptidoglycan to be degraded until the bacteria die [10]. At the same time, in addition to the mechanism by which antibiotics directly kill bacteria, the latest research has found that different types of antibiotics can cause the continuous accumulation of reactive oxygen species (reactiveoxygen species, ROS) of bacteria when stimulating bacterial stress, and finally produce or Strengthen the bactericidal effect. When β-lactam drugs act on bacteria, they will also cause the bacteria to accumulate ROS and finally achieve a lethal effect. Even ROS has the function of helping ampicillin to crack bacteria [11]. With the deepening of scientific research, there are also new discoveries in the ways of β-lactam drugs leading to bacterial death. It is possible that β-lactam drugs have multiple ways to cause bacterial death [3,8-11], but as long as one of the ways is blocked, bacterial resistance may also occur. |
Last Update：2024-04-09 20:49:11
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