Biosynthesis of the C-Glycosylated Depside Arenicolin B

被引:0
|
作者
Johnson, Colin W. [1 ]
Nuniz, Lorraine [1 ]
Perlatti, Bruno [1 ,2 ,3 ]
Bills, Gerald F. [2 ,4 ]
Tang, Yi [1 ,5 ]
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[2] Univ Texas, Brown Fdn Inst Mol Med, Texas Therapeut Inst, Hlth Sci Ctr Houston, Houston, TX 77054 USA
[3] Hexagon Bio, Menlo Pk, CA 94025 USA
[4] Rutgers State Univ, Dept Plant Biol, New Brunswick, NJ 08901 USA
[5] Univ Calif Los Angeles, Dept Chem & Biomol Engn, Los Angeles, CA 90095 USA
关键词
depside natural product; <italic>C</italic>-glycosyltransferase; glycosylated natural product; natural product biosynthesis; polyketide synthase; THIELAVIN-A; INHIBITORS;
D O I
10.1002/cbic.202500003
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
We uncovered the biosynthetic pathway of the C-glycosylated depside arenicolin B from Phialomyces arenicola through genome mining, heterologous reconstitution and biochemical characterization. The biosynthetic gene cluster (BGC) of arenicolin B is comprised of a HRPKS, a NRPKS, and a C-glycosyltransferase. Through biochemical dissection and evaluation, we demonstrate the NRPKS thioesterase (TE) domain catalyses depside formation.
引用
收藏
页数:6
相关论文
共 50 条
  • [21] Synthesis and structure-activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase
    Toth, Marietta
    Kun, Sandor
    Bokor, Eva
    Benltifa, Mahmoud
    Tallec, Gaylord
    Vidal, Sebastien
    Docsa, Tibor
    Gergely, Pal
    Somsak, Laszlo
    Praly, Jean-Pierre
    BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (13) : 4773 - 4785
  • [22] Short and stereoselective synthesis of C-glycosylated glycine derivatives from glycals by radical addition and reduction
    Sommermann, T
    Kim, BG
    Peters, K
    Peters, EM
    Linker, T
    CHEMICAL COMMUNICATIONS, 2004, (22) : 2624 - 2625
  • [23] Going beyond structural effects: explicit solvation influence on the rotational isomerism of C-glycosylated flavonoids
    de Andrade, Karine N. N.
    Martorano, Lucas H. H.
    Correa, Guilherme S. S.
    dos Santos Jr, Fernando M. M.
    Carneiro, Jose Walkimar de M.
    de Albuquerque, Ana Carolina F.
    Gomes, Anne Caroline C.
    Fiorot, Rodolfo G. G.
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (20) : 5044 - 5054
  • [24] A cytotoxic C-glycosylated derivative of apigenin from the leaves of Ocimum basilicum var. thyrsiflorum
    Mohamed I. S. Abdelhady
    Amira Abdel Motaal
    Revista Brasileira de Farmacognosia, 2016, 26 : 763 - 766
  • [25] C-Glycopyranosyl-1,4-benzoquinones and -hydroquinones opening access to C-glycosylated analogs of vitamin E
    Praly, JP
    He, L
    Qin, BB
    Tanoh, M
    Chen, GR
    TETRAHEDRON LETTERS, 2005, 46 (41) : 7081 - 7085
  • [26] A cytotoxic C-glycosylated derivative of apigenin from the leaves of Ocimum basilicium var. thyrsiflorum
    Abdelhady, Mohamed I. S.
    Motaal, Amira Abdel
    REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY, 2016, 26 (06): : 763 - 766
  • [27] Indirect and direct routes to C-glycosylated flavones in Saccharomyces cerevisiae (vol 17, 107, 2018)
    Vanegas, Katherina Garcia
    Larsen, Aresu Bondrup
    Eichenberger, Michael
    Fischer, David
    Mortensen, Uffe Hasbro
    Naesby, Michael
    MICROBIAL CELL FACTORIES, 2018, 17
  • [28] Investigation of C-glycosylated apigenin and luteolin derivatives' effects on protein tyrosine phosphatase 1B inhibition with molecular and cellular approaches
    Ali, Md Yousof
    Jannat, Susoma
    Rahman, M. Mizanur
    COMPUTATIONAL TOXICOLOGY, 2021, 17
  • [29] "Boomerang" Strategy in Carbohydrate Chemistry: Diastereoselective Synthesis of C-Glycosylated Benzothiazoles from ortho-Isocyanophenyl Thioglycosides
    Hu, Li-Yan
    Zhang, Shen-Yuan
    Zhu, Li
    Li, Yang
    Luo, Kai
    Wu, Lei
    ORGANIC LETTERS, 2023, 26 (01) : 215 - 220
  • [30] C-glycosylated phenylalanine synthesis by palladium-catalyzed cross-coupling reactions (Sept, pg 1834, 2003)
    Boucard, V
    Larrieu, K
    Lubin-Germain, N
    Uziel, J
    Augé, J
    SYNLETT, 2003, (15) : 2444 - 2444