140:, a class of enzymes that break open the β-lactam ring. More than 1,800 different β-lactamase enzymes have been documented in various species of bacteria. These enzymes vary widely in their chemical structure and catalytic efficiencies. When bacterial populations have these resistant subgroups, treatment with β-lactam can result in the resistant strain becoming more prevalent and therefore more virulent. β-lactam derived antibiotics can be considered one of the most important antibiotic classes but prone to clinical resistance. β-lactam exhibits its antibiotic properties by imitating the naturally occurring d-Ala-d-Ala substrate for the group of enzymes known as
197:
89:
27:
299:
values in of 0.20–0.25 Å. Penams have values in the range 0.40–0.50 Å, while carbapenems and clavams have values of 0.50–0.60 Å, being the most reactive of the β-lactams toward hydrolysis.
243:
than linear amides or larger lactams. This strain is further increased by fusion to a second ring, as found in most β-lactam antibiotics. This trend is due to the amide character of the β-lactam being reduced by the
224:
972:
Nangia A, Biradha K, Desiraju GR (1996). "Correlation of biological activity in β-lactam antibiotics with
Woodward and Cohen structural parameters: A Cambridge database study".
704:
Alcaide, Benito; Almendros, Pedro; Aragoncillo, Cristina (2007). "Β-Lactams: Versatile
Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products".
62:
atom relative to the carbonyl. The simplest β-lactam possible is 2-azetidinone. β-lactams are significant structural units of medicines as manifested in many
287:
corresponds to the strength of the β-lactam bond with lower numbers (more planar; more like ideal amides) being stronger and less reactive. Monobactams have
364:
Fisher, J. F.; Meroueh, S. O.; Mobashery, S. (2005). "Bacterial resistance to β-lactam antibiotics: compelling opportunism, compelling opportunity".
873:
894:
319:
264:
bond geometry is forced upon the nitrogen atom by the ring strain, the resonance of the amide bond is reduced, and the carbonyl becomes more
867:
348:
823:
257:
1002:
451:"In silico serine β-lactamases analysis reveals a huge potential resistome in environmental and pathogenic species"
148:
567:"Mechanism of action of penicillins: a proposal based on their structural similarity to acyl-D-alanyl-D-alanine"
683:
141:
144:(PBP), which have as function to cross-link the peptidoglycan part of the cell wall of the bacteria.
902:
223:
215:
63:
624:
Tidwell TT (2008). "Hugo (Ugo) Schiff, Schiff bases, and a century of beta-lactam synthesis".
117:
83:
20:
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272:
253:
249:
133:
129:
449:
Brandt C, Braun SD, Stein C, Slickers P, Ehricht R, Pletz MW, Makarewicz O (February 2017).
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8:
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Philosophical
Transactions of the Royal Society of London. Series B, Biological Sciences
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produces substituted β-lactams by the cyclization of beta amino acid esters by use of a
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Ehmann DE, Jahić H, Ross PL, Gu RF, Hu J, Kern G, Walkup GK, Fisher SL (July 2012).
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as a measure of the height of the trigonal pyramid defined by the nitrogen (as the
245:
211:
128:, although any given bacteria population will typically contain a subgroup that is
414:
Hosseyni S, Jarrahpour A (October 2018). "Recent advances in β-lactam synthesis".
788:"Chemical Synthesis of β-Lactams: Asymmetric Catalysis and Other Recent Advances"
280:
136:
occurs as a result of the expression of one of many genes for the production of
854:, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 521–524, 2010-09-15,
571:
Proceedings of the
National Academy of Sciences of the United States of America
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Proceedings of the
National Academy of Sciences of the United States of America
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This article is about the chemical compound. For the related antibiotics, see
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groups, but since then, a wide variety of structures have been described.
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508:"Avibactam is a covalent, reversible, non-β-lactam β-lactamase inhibitor"
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58:-lactams are named so because the nitrogen atom is attached to the
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Many methods have been developed for the synthesis of β-lactams.
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The β-lactam ring is also found in some other drugs such as the
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120:. Nearly all of these antibiotics work by inhibiting bacterial
43:
26:
51:
66:. Up to 1970, most β-lactam research was concerned with the
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401:
96:
The β-lactam ring is part of the core structure of several
892:
448:
739:
Hosseyni, Seyedmorteza; Jarrahpour, Aliasghar (2018).
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of the system. The nitrogen atom of an ideal amide is
971:
738:
413:
852:Comprehensive Organic Name Reactions and Reagents
505:
1009:
564:
786:Pitts, Cody Ross; Lectka, Thomas (2014-08-27).
218:is also used in modified Breckpot synthesis.
320:Lectka enantioselective beta-lactam synthesis
163:The first synthetic β-lactam was prepared by
965:
785:
407:
658:
558:
124:biosynthesis. This has a lethal effect on
948:
893:Bogdanov B, Zdravkovski Z, Hristovski K.
664:"Zur Kenntniss der Ketene. Diphenylketen"
600:
590:
565:Tipper DJ, Strominger JL (October 1965).
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482:
338:
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87:
77:
25:
741:"Recent advances in β-lactam synthesis"
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100:families, the principal ones being the
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403:. New York and London: Academic Press.
842:
840:
499:
442:
398:
745:Organic & Biomolecular Chemistry
416:Organic & Biomolecular Chemistry
116:, which are, therefore, also called
30:2-Azetidinone, the simplest β-lactam
13:
837:
291:values between 0.05 and 0.10
14:
1029:
996:
283:) and its three adjacent atoms.
222:
195:
149:cholesterol absorption inhibitor
925:"Penems and related substances"
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876:from the original on 2024-01-16
826:from the original on 2022-07-21
779:
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686:from the original on 2020-08-02
256:, and sp-hybridized atoms have
860:10.1002/9780470638859.conrr115
652:
617:
392:
357:
343:. Harlow: Longman Scientific.
332:
1:
899:Institute of Chemistry Skopje
848:"Breckpot β-Lactam Synthesis"
325:
258:trigonal planar bond geometry
239:, β-lactams are more readily
230:
158:
16:Family of chemical compounds
7:
303:
208:Breckpot β-lactam synthesis
167:in 1907 by reaction of the
142:penicillin binding proteins
10:
1034:
974:J. Chem. Soc. Perkin Trans
81:
42:) ring is a four-membered
18:
132:to β-lactam antibiotics.
92:Penicillin core structure
923:Woodward RB (May 1980).
680:10.1002/jlac.19073560106
668:Justus Liebigs Ann. Chem
533:10.1073/pnas.1205073109
1003:Synthesis of β-lactams
950:10.1098/rstb.1980.0042
638:10.1002/anie.200702965
592:10.1073/pnas.54.4.1133
341:Heterocyclic Chemistry
275:described a parameter
93:
31:
273:Robert Burns Woodward
91:
78:Clinical significance
29:
986:10.1039/p29960000943
895:"Breckpot Synthesis"
339:Gilchrist T (1987).
134:Bacterial resistance
118:β-lactam antibiotics
64:β-lactam antibiotics
941:1980RSPTB.289..239W
583:1965PNAS...54.1133T
524:2012PNAS..10911663E
467:2017NatSR...743232B
216:Mukaiyama's reagent
191:functional group):
84:β-Lactam antibiotic
21:β-Lactam antibiotic
757:10.1039/C8OB01833B
455:Scientific Reports
428:10.1039/c8ob01833b
295:(Å). Cephems have
165:Hermann Staudinger
94:
32:
869:978-0-470-63885-9
804:10.1021/cr4005549
798:(16): 7930–7953.
751:(38): 6840–6852.
718:10.1021/cr0307300
712:(11): 4437–4492.
626:Angewandte Chemie
475:10.1038/srep43232
422:(38): 6840–6852.
399:Flynn EH (1972).
378:10.1021/cr030102i
350:978-0-582-01421-3
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181:diphenylketene
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106:cephalosporins
82:Main article:
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1018:Beta-lactams
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907:. Retrieved
903:the original
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851:
828:. Retrieved
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177:benzaldehyde
162:
146:
138:β-lactamases
95:
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50:is a cyclic
47:
39:
35:
33:
237:ring strain
169:Schiff base
114:monobactams
110:carbapenems
102:penicillins
36:beta-lactam
909:2014-12-30
880:2021-02-04
830:2020-12-17
690:2019-06-27
326:References
246:aplanarity
241:hydrolyzed
98:antibiotic
68:penicillin
812:0009-2665
765:1477-0520
461:: 43232.
310:Azetidine
293:angstroms
262:pyramidal
254:resonance
231:Reactions
159:Synthesis
153:ezetimibe
130:resistant
122:cell wall
1012:Category
874:archived
824:Archived
820:24555548
773:30209477
726:17649981
684:Archived
662:(1907).
646:18022986
552:22753474
493:28233789
436:30209477
386:15700950
304:See also
126:bacteria
60:β-carbon
40:β-lactam
959:6109320
937:Bibcode
611:5219821
579:Bibcode
543:3406822
520:Bibcode
484:5324141
463:Bibcode
315:Lactone
268:-like.
260:. As a
252:due to
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112:, and
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179:with
151:drug
52:amide
955:PMID
864:ISBN
816:PMID
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761:ISSN
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642:PMID
607:PMID
548:PMID
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432:PMID
382:PMID
345:ISBN
281:apex
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