Biosynthesis of sulfonamide and sulfamate antibiotics in actinomycete.


Journal

Journal of industrial microbiology & biotechnology
ISSN: 1476-5535
Titre abrégé: J Ind Microbiol Biotechnol
Pays: Germany
ID NLM: 9705544

Informations de publication

Date de publication:
04 Jun 2021
Historique:
accepted: 21 11 2020
received: 28 09 2020
pubmed: 1 5 2021
medline: 20 7 2021
entrez: 30 4 2021
Statut: ppublish

Résumé

Sulfonamides and sulfamates are a group of organosulfur compounds that contain the signature sulfamoyl structural motif. These compounds were initially only known as synthetic antibacterial drugs but were later also discovered as natural products. Eight highly potent examples have been isolated from actinomycetes to date, illustrating the large biosynthetic repertoire of this bacterial genus. For the biosynthesis of these compounds, several distinct and unique biosynthetic machineries have been discovered, capable to generate the unique S-N bond. For the creation of novel, second generation natural products by biosynthetic engineering efforts, a detailed understanding of the underlying enzyme machinery toward potent structural motifs is crucial. In this review, we aim to summarize the current state of knowledge on sulfonamide and sulfamate biosynthesis. A detailed discussion for the secondary sulfamate ascamycin, the tertiary sulfonamide sulfadixiamycin A, and the secondary sulfonamide SB-203208 is provided and their bioactivities and mode of actions are discussed.

Identifiants

pubmed: 33928358
pii: 6123731
doi: 10.1093/jimb/kuab001
pmc: PMC9113183
pii:
doi:

Substances chimiques

Anti-Bacterial Agents 0
Biological Products 0
Sulfonamides 0
Sulfonic Acids 0
sulfamic acid 9NFU33906Q

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Informations de copyright

© The Author(s) 2021. Published by Oxford University Press on behalf of Society of Industrial Microbiology and Biotechnology.

Références

Chembiochem. 2015 Nov;16(17):2498-506
pubmed: 26374477
Chembiochem. 2009 Oct 12;10(15):2480-7
pubmed: 19731276
Chem Sci. 2019 Aug 20;10(41):9501-9505
pubmed: 32110306
Nature. 2018 Jul;559(7714):415-418
pubmed: 29995859
J Antibiot (Tokyo). 1989 Nov;42(11):1556-61
pubmed: 2584137
Immunol Today. 1999 Aug;20(8):367-75
pubmed: 10431157
PLoS One. 2014 Dec 05;9(12):e114722
pubmed: 25479601
Biol Chem. 1997 Mar-Apr;378(3-4):193-7
pubmed: 9165070
Org Biomol Chem. 2017 Oct 4;15(38):8006-8008
pubmed: 28920128
J Antibiot (Tokyo). 2000 Apr;53(4):364-72
pubmed: 10866218
Arch Biochem Biophys. 2001 Jun 15;390(2):149-57
pubmed: 11396917
Biochem J. 1986 Jan 15;233(2):459-63
pubmed: 3754135
J Am Chem Soc. 1969 Mar 12;91(6):1535-7
pubmed: 5776261
Bull World Health Organ. 1977;55(2-3):291-8
pubmed: 338184
ACS Chem Biol. 2015 Dec 18;10(12):2841-2849
pubmed: 26458099
Chemistry. 2017 Aug 10;23(45):10714-10724
pubmed: 28488371
Amino Acids. 2011 Jun;41(1):91-102
pubmed: 20195658
J Antibiot (Tokyo). 2001 Sep;54(9):744-6
pubmed: 11714231
J Antibiot (Tokyo). 2000 Apr;53(4):357-63
pubmed: 10866217
J Biol Chem. 1966 Mar 10;241(5):1091-8
pubmed: 5933868
EMBO J. 2000 Dec 1;19(23):6299-310
pubmed: 11101502
Angew Chem Int Ed Engl. 2012 Oct 8;51(41):10293-7
pubmed: 22968942
Nat Commun. 2019 Jan 14;10(1):184
pubmed: 30643149
J Antibiot (Tokyo). 1984 Jun;37(6):670-2
pubmed: 6547710
Nat Prod Rep. 2020 Jul 1;37(7):879-892
pubmed: 31912842
J Antibiot (Tokyo). 1989 Nov;42(11):1562-6
pubmed: 2584138
Antimicrob Agents Chemother. 1985 Feb;27(2):230-3
pubmed: 2580481
Bioorg Med Chem Lett. 2010 Nov 15;20(22):6685-7
pubmed: 20880706
J Antibiot (Tokyo). 1982 Aug;35(8):939-47
pubmed: 7142012
Angew Chem Int Ed Engl. 2013 Aug 19;52(34):9040-3
pubmed: 23843280
Biochemistry. 2019 Apr 30;58(17):2218-2227
pubmed: 30946568
J Nat Prod. 2018 Feb 23;81(2):423-446
pubmed: 29364663
J Am Chem Soc. 2012 May 30;134(21):8996-9005
pubmed: 22591327
Angew Chem Int Ed Engl. 2015 Nov 2;54(45):13279-83
pubmed: 26366473
Chem Rev. 2017 Apr 26;117(8):5784-5863
pubmed: 28375000
Chem Sci. 2017 Jul 1;8(7):5067-5077
pubmed: 28970893
Nature. 2002 Mar 21;416(6878):279
pubmed: 11907567

Auteurs

Takayoshi Awakawa (T)

Graduate School of Pharmaceutical Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan.
Collaborative Research Institute for Innovative Microbiology, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113-8657, Japan.

Lena Barra (L)

Graduate School of Pharmaceutical Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan.

Ikuro Abe (I)

Graduate School of Pharmaceutical Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan.
Collaborative Research Institute for Innovative Microbiology, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113-8657, Japan.

Articles similaires

Vancomycin-associated DRESS demonstrates delay in AST abnormalities.

Ahmed Hussein, Kateri L Schoettinger, Jourdan Hydol-Smith et al.
1.00
Humans Drug Hypersensitivity Syndrome Vancomycin Female Male
Humans Arthroplasty, Replacement, Elbow Prosthesis-Related Infections Debridement Anti-Bacterial Agents
Vancomycin Polyesters Anti-Bacterial Agents Models, Theoretical Drug Liberation
Humans China Cerebral Hemorrhage Patient Care Bundles Length of Stay

Classifications MeSH