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  1. Article ; Online: Modifications of Protein-Bound Substrates by Trans-Acting Enzymes in Natural Products Biosynthesis.

    Skala, Leigh E / Philmus, Benjamin / Mahmud, Taifo

    Chembiochem : a European journal of chemical biology

    2024  Volume 25, Issue 8, Page(s) e202400056

    Abstract: Enzymatic modifications of small molecules are a common phenomenon in natural product biosynthesis, leading to the production of diverse bioactive compounds. In polyketide biosynthesis, modifications commonly take place after the completion of the ... ...

    Abstract Enzymatic modifications of small molecules are a common phenomenon in natural product biosynthesis, leading to the production of diverse bioactive compounds. In polyketide biosynthesis, modifications commonly take place after the completion of the polyketide backbone assembly by the polyketide synthases and the mature products are released from the acyl-carrier protein (ACP). However, exceptions to this rule appear to be widespread, as on-line hydroxylation, methyl transfer, and cyclization during polyketide assembly process are common, particularly in trans-AT PKS systems. Many of these modifications are catalyzed by specific domains within the modular PKS systems. However, several of the on-line modifications are catalyzed by stand-alone proteins. Those include the on-line Baeyer-Villiger oxidation, α-hydroxylation, halogenation, epoxidation, and methyl esterification during polyketide assembly, dehydrogenation of ACP-bound short fatty acids by acyl-CoA dehydrogenase-like enzymes, and glycosylation of ACP-bound intermediates by discrete glycosyltransferase enzymes. This review article highlights some of these trans-acting proteins that catalyze enzymatic modifications of ACP-bound small molecules in natural product biosynthesis.
    MeSH term(s) Polyketide Synthases/metabolism ; Acyl Carrier Protein/chemistry ; Polyketides/chemistry
    Chemical Substances Polyketide Synthases (79956-01-7) ; Acyl Carrier Protein ; Polyketides
    Language English
    Publishing date 2024-03-11
    Publishing country Germany
    Document type Journal Article ; Review
    ZDB-ID 2020469-3
    ISSN 1439-7633 ; 1439-4227
    ISSN (online) 1439-7633
    ISSN 1439-4227
    DOI 10.1002/cbic.202400056
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  2. Article ; Online: Molecular basis for the increased activity of ZMS-2 serine protease in the presence of metal ions and hydrogen peroxide.

    Khan, Zahoor / Tanoeyadi, Samuel / Jabeen, Nusrat / Shafique, Maryam / Naz, Sehar Afshan / Mahmud, Taifo

    Journal of inorganic biochemistry

    2024  Volume 256, Page(s) 112566

    Abstract: Serine proteases are important enzymes widely used in commercial products and industry. Recently, we identified a new serine protease from the desert bacterium Bacillus subtilis ZMS-2 that showed enhanced activity in the presence of ... ...

    Abstract Serine proteases are important enzymes widely used in commercial products and industry. Recently, we identified a new serine protease from the desert bacterium Bacillus subtilis ZMS-2 that showed enhanced activity in the presence of Zn
    Language English
    Publishing date 2024-04-21
    Publishing country United States
    Document type Journal Article
    ZDB-ID 162843-4
    ISSN 1873-3344 ; 0162-0134
    ISSN (online) 1873-3344
    ISSN 0162-0134
    DOI 10.1016/j.jinorgbio.2024.112566
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  3. Article ; Online: Synthesis of the Carba-Analogs of the α-Pyranose and β-Pyranose Forms of Sedoheptulose 7-Phosphate and Probing the Stereospecificity of Sedoheptulose 7-Phosphate Cyclases.

    Samadi, Arash / Tanoeyadi, Samuel / Tsunoda, Takeshi / Proteau, Philip J / Mahmud, Taifo

    Biochemistry

    2024  

    Abstract: Sedoheptulose 7-phosphate (SH7P) cyclases are a subset of sugar phosphate cyclases that are known to catalyze the first committed step in many biosynthetic pathways in primary and secondary metabolism. Among them are 2- ...

    Abstract Sedoheptulose 7-phosphate (SH7P) cyclases are a subset of sugar phosphate cyclases that are known to catalyze the first committed step in many biosynthetic pathways in primary and secondary metabolism. Among them are 2-
    Language English
    Publishing date 2024-04-30
    Publishing country United States
    Document type Journal Article
    ZDB-ID 1108-3
    ISSN 1520-4995 ; 0006-2960
    ISSN (online) 1520-4995
    ISSN 0006-2960
    DOI 10.1021/acs.biochem.4c00034
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  4. Article ; Online: EDB Gene Cluster-Dependent Indole Production Is Responsible for the Ability of

    Zhou, Wei / Vergis, John / Mahmud, Taifo

    Journal of natural products

    2022  Volume 85, Issue 3, Page(s) 590–598

    Abstract: The "EDB" (from "edible") gene cluster, a variant of the ebo cluster of genes found in many bacteria and algae, ... ...

    Abstract The "EDB" (from "edible") gene cluster, a variant of the ebo cluster of genes found in many bacteria and algae, allows
    MeSH term(s) Aldehydes/metabolism ; Animals ; Caenorhabditis elegans/metabolism ; Escherichia coli/genetics ; Escherichia coli/metabolism ; Indoles/metabolism ; Indoles/pharmacology ; Multigene Family ; Pseudomonas fluorescens/genetics ; Tryptophan/metabolism
    Chemical Substances Aldehydes ; Indoles ; indole (8724FJW4M5) ; Tryptophan (8DUH1N11BX)
    Language English
    Publishing date 2022-01-25
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.1c01046
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  5. Article ; Online: Biochemical Characterization of GacI, a Bifunctional Glycosyltransferase-Phosphatase Enzyme Involved in Acarbose Biosynthesis in

    Tsunoda, Takeshi / Asamizu, Shumpei / Mahmud, Taifo

    Biochemistry

    2022  Volume 61, Issue 22, Page(s) 2628–2635

    Abstract: Acarbose, a pseudotetrasaccharide produced by several strains ... ...

    Abstract Acarbose, a pseudotetrasaccharide produced by several strains of
    MeSH term(s) Humans ; Acarbose/metabolism ; Glycosyltransferases/genetics ; Glycosyltransferases/metabolism ; Phosphoric Monoester Hydrolases/metabolism ; Diabetes Mellitus, Type 2 ; Bacterial Proteins/genetics ; Bacterial Proteins/metabolism ; Streptomyces/genetics ; Streptomyces/metabolism
    Chemical Substances Acarbose (T58MSI464G) ; Glycosyltransferases (EC 2.4.-) ; Phosphoric Monoester Hydrolases (EC 3.1.3.2) ; Bacterial Proteins
    Language English
    Publishing date 2022-10-26
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 1108-3
    ISSN 1520-4995 ; 0006-2960
    ISSN (online) 1520-4995
    ISSN 0006-2960
    DOI 10.1021/acs.biochem.2c00473
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  6. Article ; Online: Acarbose May Function as a Competitive Exclusion Agent for the Producing Bacteria.

    Tanoeyadi, Samuel / Tsunoda, Takeshi / Ito, Takuya / Philmus, Benjamin / Mahmud, Taifo

    ACS chemical biology

    2023  Volume 18, Issue 2, Page(s) 367–376

    Abstract: Acarbose is a well-known microbial specialized metabolite used clinically to treat type 2 diabetes. This natural pseudo-oligosaccharide (PsOS) shows potent inhibitory activity toward various glycosyl hydrolases, including α-glucosidases and α-amylases. ... ...

    Abstract Acarbose is a well-known microbial specialized metabolite used clinically to treat type 2 diabetes. This natural pseudo-oligosaccharide (PsOS) shows potent inhibitory activity toward various glycosyl hydrolases, including α-glucosidases and α-amylases. While acarbose and other PsOSs are produced by many different bacteria, their ecological or biological role in microbial communities is still an open question. Here, we show that several PsOS-producing actinobacteria, i.e.,
    MeSH term(s) Humans ; Acarbose ; Diabetes Mellitus, Type 2 ; Bacterial Proteins/metabolism ; Actinobacteria/metabolism ; alpha-Amylases/metabolism
    Chemical Substances Acarbose (T58MSI464G) ; Bacterial Proteins ; alpha-Amylases (EC 3.2.1.1)
    Language English
    Publishing date 2023-01-17
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ISSN 1554-8937
    ISSN (online) 1554-8937
    DOI 10.1021/acschembio.2c00795
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  7. Article ; Online: Complete biosynthetic pathway to the antidiabetic drug acarbose

    Takeshi Tsunoda / Arash Samadi / Sachin Burade / Taifo Mahmud

    Nature Communications, Vol 13, Iss 1, Pp 1-

    2022  Volume 12

    Abstract: The market demand for acarbose, a drug used for treatment of patients affected by type-2 diabetes, has increased. In this article, the authors report the acarbose complete biosynthetic pathway, clarifying previously unknown steps and identifying a ... ...

    Abstract The market demand for acarbose, a drug used for treatment of patients affected by type-2 diabetes, has increased. In this article, the authors report the acarbose complete biosynthetic pathway, clarifying previously unknown steps and identifying a pseudoglycosyltransferase enzyme, AcbS, a homologue of AcbI that catalyzes the formation of a non-glycosidic C-N bond.
    Keywords Science ; Q
    Language English
    Publishing date 2022-06-01T00:00:00Z
    Publisher Nature Portfolio
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  8. Article ; Online: The chemistry and biology of natural ribomimetics and related compounds.

    Tsunoda, Takeshi / Tanoeyadi, Samuel / Proteau, Philip J / Mahmud, Taifo

    RSC chemical biology

    2022  Volume 3, Issue 5, Page(s) 519–538

    Abstract: Natural ribomimetics represent an important group of specialized metabolites with significant biological activities. Many of the activities, ...

    Abstract Natural ribomimetics represent an important group of specialized metabolites with significant biological activities. Many of the activities,
    Language English
    Publishing date 2022-04-07
    Publishing country England
    Document type Journal Article ; Review
    ISSN 2633-0679
    ISSN (online) 2633-0679
    DOI 10.1039/d2cb00019a
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  9. Article ; Online: Modifications of Acyl Carrier Protein-Bound Glycosylated Polyketides in Pactamycin Biosynthesis.

    Eida, Auday A / Samadi, Arash / Tsunoda, Takeshi / Mahmud, Taifo

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2023  Volume 29, Issue 33, Page(s) e202301056

    Abstract: The potent antitumor antibiotic pactamycin is an aminocyclopentitol-containing natural product produced by the soil bacterium Streptomyces pactum. Recent studies showed that the aminocyclopentitol unit is derived from N-acetyl-D-glucosamine, which is ... ...

    Abstract The potent antitumor antibiotic pactamycin is an aminocyclopentitol-containing natural product produced by the soil bacterium Streptomyces pactum. Recent studies showed that the aminocyclopentitol unit is derived from N-acetyl-D-glucosamine, which is attached to an acyl carrier protein (ACP)-bound polyketide by a glycosyltransferase enzyme, PtmJ. Here, we report a series of post-glycosylation modifications of the sugar moiety of the glycosylated polyketide while it is still attached to the carrier protein. In vitro reconstitution of PtmS (an AMP-ligase), PtmI (an ACP), PtmJ, PtmN (an oxidoreductase), PtmA (an aminotransferase), and PtmB (a putative carbamoyltransferase) showed that the N-acetyl-D-glucosamine moiety of the glycosylated polyketide is first oxidized by PtmN and then transaminated by PtmA to give ACP-bound 3-amino-3-deoxy-N-acetyl-D-glucosaminyl polyketide. The amino group is then coupled with carbamoyl phosphate by PtmB to give a urea functionality. We also show that PtmG is a deacetylase that hydrolyses the C-2 N-acetyl group to give a free amine.
    MeSH term(s) Pactamycin ; Acyl Carrier Protein ; Glycosylation ; Polyketides ; Acetylglucosamine
    Chemical Substances Pactamycin (23668-11-3) ; Acyl Carrier Protein ; 3-hydroxyphenyltrimethylammonium (3483-84-9) ; Polyketides ; Acetylglucosamine (V956696549)
    Language English
    Publishing date 2023-04-26
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202301056
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  10. Article ; Online: Four sulfur-containing compounds with anti-colon cancer effect from marine-derived fungus Aspergillus terreus.

    Zhang, Guang-Yu / Liu, Bei-Jia / Pan, Hui-Lin / Li, Hou-Jin / Huang, Zi-Feng / Mahmud, Taifo / Ma, Wen-Zhe / Lan, Wen-Jian

    Fitoterapia

    2024  Volume 175, Page(s) 105967

    Abstract: Sulfur-containing natural products possess a variety of biological functions including antitumor, antibacterial, anti-inflammatory and antiviral activities. In this study, four previously undescribed sulfur-containing compounds asperteretals L and M, ... ...

    Abstract Sulfur-containing natural products possess a variety of biological functions including antitumor, antibacterial, anti-inflammatory and antiviral activities. In this study, four previously undescribed sulfur-containing compounds asperteretals L and M, terreins A and B, together with 17 known compounds were obtained from a culture of marine fungus A. terreus supplemented with inorganic sulfur source Na
    Language English
    Publishing date 2024-04-16
    Publishing country Netherlands
    Document type Journal Article
    ZDB-ID 412385-2
    ISSN 1873-6971 ; 0367-326X
    ISSN (online) 1873-6971
    ISSN 0367-326X
    DOI 10.1016/j.fitote.2024.105967
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