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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/21 22:04:24」(JST)

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From left to right, general structures of a β-lactam, a γ-lactam, a δ-lactam and an ε-lactam.

A lactam (the noun is a portmanteau of the words lactone + amide) is a cyclic amide. Prefixes indicate how many carbon atoms (apart from the carbonyl moiety) are present in the ring: β-lactam (2 carbon atoms outside the carbonyl, 4 ring atoms in total), γ-lactam (3 and 5 total), δ-lactam (4 and 6 total). Beta β, gamma γ and delta δ are the second, third and fourth letters in the alphabetical order of the Greek alphabet, respectively.

Synthesis

General synthetic methods exist for the organic synthesis of lactams.

Lactams form by the acid-catalyzed rearrangement of oximes in the Beckmann rearrangement.
Lactams form from cyclic ketones and hydrazoic acid in the Schmidt reaction.
Lactams form from cyclisation of amino acids.
Lactams form from intramolecular attack of linear acyl derivatives from the nucleophilic abstraction reaction.
In iodolactamization ^[1] an iminium ion reacts with an halonium ion formed in situ by reaction of an alkene with iodine.

Lactams form by copper catalyzed 1,3-dipolar cycloaddition of alkynes and nitrones in the Kinugasa reaction
Diels-Alder reaction between cyclopentadiene and chlorosulfonyl isocyanate (CSI) can be utilized to obtain both β- as well as γ-lactam. At lower temp (−78 °C) β-lactam is the preferred product. At optimum temperatures, a highly useful γ-lactam known as Vince Lactam is obtained.^[2]

Tautomerization to Lactim

Lactim is a cyclic carboximidic acid compound characterized by an endocyclic carbon-nitrogen double bond. It is formed when lactam undergoes tautomerization.

Reactions

Lactams can polymerize to polyamides.

References

^ Spencer Knapp, Frank S. Gibson Organic Syntheses, Coll. Vol. 9, p.516 (1998); Vol. 70, p.101 (1992) Online article
^ Pham, P.-T.; Vince, R. Phosphorus, Sulphur and Silicon 2007, 779-791.

UpToDate Contents

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1. β-ラクタム系抗生物質：作用機序、耐性および有害作用 beta lactam antibiotics mechanisms of action and resistance and adverse effects
2. 基質特異性拡張型β-ラクタマーゼ extended spectrum beta lactamases
3. ペニシリン penicillins
4. β-ラクタマーゼ阻害剤、カルバペネム系、およびモノバクタム系抗菌薬の併用 combination beta lactamase inhibitors carbapenems and monobactams
5. 成人における市中肺炎の治療に関する抗菌薬の研究 antibiotic studies for the treatment of community acquired pneumonia in adults

English Journal

Prevalence of antibiotic resistance genes and their relationship with antibiotics in the Huangpu River and the drinking water sources, Shanghai, China.

Jiang L, Hu X, Xu T, Zhang H, Sheng D, Yin D.SourceKey Laboratory of Yangtze River Water Environment, Ministry of Education, College of Environmental Science and Engineering, Tongji University, Shanghai 200092, China; Municipal Water Resource Development and Utilization (South) National Engineering Research Center, Shanghai 200082, China.
The Science of the total environment.Sci Total Environ.2013 Aug 1;458-460:267-72. doi: 10.1016/j.scitotenv.2013.04.038. Epub 2013 May 7.
The prevalence of antibiotic resistance genes (ARGs) and their relationship with antibiotics in the surface waters of the Huangpu River and the drinking water sources of Shanghai, China, were investigated. 39 ARGs, including four sulfonamide ARGs, 23 tetracycline ARGs, four chloramphenicol ARGs, fiv
PMID 23664984

Australian marine sponge alkaloids as a new class of glycine-gated chloride channel receptor modulator.

Balansa W, Islam R, Gilbert DF, Fontaine F, Xiao X, Zhang H, Piggott AM, Lynch JW, Capon RJ.SourceInstitute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia.
Bioorganic & medicinal chemistry.Bioorg Med Chem.2013 Jul 15;21(14):4420-5. doi: 10.1016/j.bmc.2013.04.061. Epub 2013 May 1.
Chemical analysis of a specimen of the sponge Ianthella cf. flabelliformis returned two new sesquiterpene glycinyl lactams, ianthellalactams A (1) and B (2), the known sponge sesquiterpene dictyodendrillin (3) and its ethanolysis artifact ethyl dictyodendrillin (4), and five known sponge indole alka
PMID 23685178

Beta-lactamase-producing Enterobacteriaceae in hospital effluents.

Korzeniewska E, Harnisz M.SourceDepartment of Environmental Microbiology, Faculty of Environmental Sciences, University of Warmia and Mazury in Olsztyn, Prawocheńskiego 1, 10-957 Olsztyn, Poland. Electronic address: ewa.korzeniewska@uwm.edu.pl.
Journal of environmental management.J Environ Manage.2013 Jul 15;123:1-7. doi: 10.1016/j.jenvman.2013.03.024. Epub 2013 Apr 9.
Beta-lactams are widely used to treat bacterial infections in humans. In most countries, they are the largest group of antibiotics used by hospitals to treat infections caused by Gram-negative bacteria. Enterobacteriaceae, natural microbiota of the human gastrointestinal tract, represent a large par
PMID 23563146

Japanese Journal

Clinical Characteristics of Tertiary Hospital Patients from Whom Acinetobacter calcoaceticus-Acinetobacter baumannii Complex Strains were Isolated

Yamada Koichi,Yanagihara Katsunori,Araki Nobuko,Harada Yosuke,Morinaga Yoshitomo,Akamatsu Norihiko,Matsuda Junichi,Izumikawa Koichi,Kakeya Hiroshi,Yamamoto Yoshihiro,Hasegawa Hiroo,Kohno Shigeru,Kamihira Shimeru
Internal Medicine 51(1), 51-57, 2012-01-01
… Approximately 60% of infected patients were treated with β-lactam agent in combination with β-lactamase inhibitors or carbapenems. …
NAID 120003725891

符号理論を用いた薬剤耐性菌の金属トランスポーター遺伝子の同定

佐藤勲興,權娟大,宮崎智
情報処理学会研究報告. BIO, バイオ情報学 2011-BIO-27(11), 1-6, 2011-11-24
… グラム陰性桿菌である Stenotrophomonas maltophilia は、抗生物質の β-lactam 環を破壊する β-ラクタマーゼ酵素を産生することで、抗生物質の効果を無力化する。 …
NAID 110008694773

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★リンクテーブル★

リンク元	「ラクタム」「ラクタム系」
拡張検索	「beta-lactam antibiotic」「プラスミド型AmpC beta-lactamase」「metallo-β-lactamase」