Cometabolic biotransformation and microbial-mediated abiotic transformation of sulfonamides by three ammonia oxidizers

Li-Jun Zhou, Ping Han, Yaochun Yu, Baozhan Wang, Yuijie Men, Michael Wagner, Qinglong Wu

Research output: Contribution to journalJournal articleResearchpeer-review

2 Citations (Scopus)

Abstract

The abilities of three phylogenetically distant ammonia oxidizers, Nitrososphaera gargensis, an ammonia-oxidizing archaeon (AOA); Nitrosomomas nitrosa Nm90, an ammonia-oxidizing bacterium (AOB); and Nitrospira inopinata, the only complete ammonia oxidizer (comammox)available as a pure culture, to biotransform seven sulfonamides (SAs)were investigated. The removals and protein-normalized biotransformation rate constants indicated that the AOA strain N. gargensis exhibited the highest SA biotransformation rates, followed by N. inopinata and N. nitrosa Nm90. The transformation products (TPs)of sulfadiazine (SDZ), sulfamethazine (SMZ)and sulfamethoxazole (SMX)and the biotransformation mechanisms were evaluated. Based on the analysis of the TP formulas and approximate structures, it was found that during biotransformation, i)the AOA strain carried out SA deamination, hydroxylation, and nitration; ii)the AOB strain mainly performed SA deamination; and iii)the comammox isolate participated only in deamination reactions. It is proposed that deamination was catalyzed by deaminases while hydroxylation and nitration were mediated by nonspecific activities of the ammonia monooxygenase (AMO). Additionally, it was demonstrated that among the three ammonia oxidizers, only AOB contributed to the formation of pterin-SA conjugates. The biotransformation of SDZ, SMZ and SMX occurred only when ammonia oxidation was active, suggesting a cometabolic transformation mechanism. Interestingly, SAs could also be transformed by hydroxylamine, an intermediate of ammonia oxidation, suggesting that in addition to enzymatic conversions, a microbially induced abiotic mechanism contributes to SA transformation during ammonia oxidation. Overall, using experiments with pure cultures, this study provides important insights into the roles played by ammonia oxidizers in SA biotransformation.

Original languageEnglish
JournalWater Research
Volume159
Pages (from-to)444-453
Number of pages10
ISSN0043-1354
DOIs
Publication statusPublished - 2019

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biotransformation
Ammonia
ammonia
Nitration
Bacteria
Hydroxylation
Sulfonamides
Biotransformation
oxidation
Oxidation
bacterium
Rate constants

Cite this

Zhou, Li-Jun ; Han, Ping ; Yu, Yaochun ; Wang, Baozhan ; Men, Yuijie ; Wagner, Michael ; Wu, Qinglong . / Cometabolic biotransformation and microbial-mediated abiotic transformation of sulfonamides by three ammonia oxidizers. In: Water Research. 2019 ; Vol. 159. pp. 444-453.
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title = "Cometabolic biotransformation and microbial-mediated abiotic transformation of sulfonamides by three ammonia oxidizers",
abstract = "The abilities of three phylogenetically distant ammonia oxidizers, Nitrososphaera gargensis, an ammonia-oxidizing archaeon (AOA); Nitrosomomas nitrosa Nm90, an ammonia-oxidizing bacterium (AOB); and Nitrospira inopinata, the only complete ammonia oxidizer (comammox)available as a pure culture, to biotransform seven sulfonamides (SAs)were investigated. The removals and protein-normalized biotransformation rate constants indicated that the AOA strain N. gargensis exhibited the highest SA biotransformation rates, followed by N. inopinata and N. nitrosa Nm90. The transformation products (TPs)of sulfadiazine (SDZ), sulfamethazine (SMZ)and sulfamethoxazole (SMX)and the biotransformation mechanisms were evaluated. Based on the analysis of the TP formulas and approximate structures, it was found that during biotransformation, i)the AOA strain carried out SA deamination, hydroxylation, and nitration; ii)the AOB strain mainly performed SA deamination; and iii)the comammox isolate participated only in deamination reactions. It is proposed that deamination was catalyzed by deaminases while hydroxylation and nitration were mediated by nonspecific activities of the ammonia monooxygenase (AMO). Additionally, it was demonstrated that among the three ammonia oxidizers, only AOB contributed to the formation of pterin-SA conjugates. The biotransformation of SDZ, SMZ and SMX occurred only when ammonia oxidation was active, suggesting a cometabolic transformation mechanism. Interestingly, SAs could also be transformed by hydroxylamine, an intermediate of ammonia oxidation, suggesting that in addition to enzymatic conversions, a microbially induced abiotic mechanism contributes to SA transformation during ammonia oxidation. Overall, using experiments with pure cultures, this study provides important insights into the roles played by ammonia oxidizers in SA biotransformation.",
author = "Li-Jun Zhou and Ping Han and Yaochun Yu and Baozhan Wang and Yuijie Men and Michael Wagner and Qinglong Wu",
year = "2019",
doi = "10.1016/j.watres.2019.05.031",
language = "English",
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pages = "444--453",
journal = "Water Research",
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Cometabolic biotransformation and microbial-mediated abiotic transformation of sulfonamides by three ammonia oxidizers. / Zhou, Li-Jun; Han, Ping; Yu, Yaochun; Wang, Baozhan; Men, Yuijie; Wagner, Michael; Wu, Qinglong .

In: Water Research, Vol. 159, 2019, p. 444-453.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Cometabolic biotransformation and microbial-mediated abiotic transformation of sulfonamides by three ammonia oxidizers

AU - Zhou, Li-Jun

AU - Han, Ping

AU - Yu, Yaochun

AU - Wang, Baozhan

AU - Men, Yuijie

AU - Wagner, Michael

AU - Wu, Qinglong

PY - 2019

Y1 - 2019

N2 - The abilities of three phylogenetically distant ammonia oxidizers, Nitrososphaera gargensis, an ammonia-oxidizing archaeon (AOA); Nitrosomomas nitrosa Nm90, an ammonia-oxidizing bacterium (AOB); and Nitrospira inopinata, the only complete ammonia oxidizer (comammox)available as a pure culture, to biotransform seven sulfonamides (SAs)were investigated. The removals and protein-normalized biotransformation rate constants indicated that the AOA strain N. gargensis exhibited the highest SA biotransformation rates, followed by N. inopinata and N. nitrosa Nm90. The transformation products (TPs)of sulfadiazine (SDZ), sulfamethazine (SMZ)and sulfamethoxazole (SMX)and the biotransformation mechanisms were evaluated. Based on the analysis of the TP formulas and approximate structures, it was found that during biotransformation, i)the AOA strain carried out SA deamination, hydroxylation, and nitration; ii)the AOB strain mainly performed SA deamination; and iii)the comammox isolate participated only in deamination reactions. It is proposed that deamination was catalyzed by deaminases while hydroxylation and nitration were mediated by nonspecific activities of the ammonia monooxygenase (AMO). Additionally, it was demonstrated that among the three ammonia oxidizers, only AOB contributed to the formation of pterin-SA conjugates. The biotransformation of SDZ, SMZ and SMX occurred only when ammonia oxidation was active, suggesting a cometabolic transformation mechanism. Interestingly, SAs could also be transformed by hydroxylamine, an intermediate of ammonia oxidation, suggesting that in addition to enzymatic conversions, a microbially induced abiotic mechanism contributes to SA transformation during ammonia oxidation. Overall, using experiments with pure cultures, this study provides important insights into the roles played by ammonia oxidizers in SA biotransformation.

AB - The abilities of three phylogenetically distant ammonia oxidizers, Nitrososphaera gargensis, an ammonia-oxidizing archaeon (AOA); Nitrosomomas nitrosa Nm90, an ammonia-oxidizing bacterium (AOB); and Nitrospira inopinata, the only complete ammonia oxidizer (comammox)available as a pure culture, to biotransform seven sulfonamides (SAs)were investigated. The removals and protein-normalized biotransformation rate constants indicated that the AOA strain N. gargensis exhibited the highest SA biotransformation rates, followed by N. inopinata and N. nitrosa Nm90. The transformation products (TPs)of sulfadiazine (SDZ), sulfamethazine (SMZ)and sulfamethoxazole (SMX)and the biotransformation mechanisms were evaluated. Based on the analysis of the TP formulas and approximate structures, it was found that during biotransformation, i)the AOA strain carried out SA deamination, hydroxylation, and nitration; ii)the AOB strain mainly performed SA deamination; and iii)the comammox isolate participated only in deamination reactions. It is proposed that deamination was catalyzed by deaminases while hydroxylation and nitration were mediated by nonspecific activities of the ammonia monooxygenase (AMO). Additionally, it was demonstrated that among the three ammonia oxidizers, only AOB contributed to the formation of pterin-SA conjugates. The biotransformation of SDZ, SMZ and SMX occurred only when ammonia oxidation was active, suggesting a cometabolic transformation mechanism. Interestingly, SAs could also be transformed by hydroxylamine, an intermediate of ammonia oxidation, suggesting that in addition to enzymatic conversions, a microbially induced abiotic mechanism contributes to SA transformation during ammonia oxidation. Overall, using experiments with pure cultures, this study provides important insights into the roles played by ammonia oxidizers in SA biotransformation.

U2 - 10.1016/j.watres.2019.05.031

DO - 10.1016/j.watres.2019.05.031

M3 - Journal article

VL - 159

SP - 444

EP - 453

JO - Water Research

JF - Water Research

SN - 0043-1354

ER -