Details
| Original language | English |
|---|---|
| Pages (from-to) | 4163-4167 |
| Number of pages | 5 |
| Journal | Organic Letters |
| Volume | 21 |
| Issue number | 11 |
| Early online date | 17 May 2019 |
| Publication status | Published - 7 Jun 2019 |
Abstract
The biosynthetic gene cluster encoding the phytotoxin pyrichalasin H 5 was discovered in Magnaporthe grisea NI980, and the late-stage biosynthetic pathway of 5 was fully elucidated using targeted gene inactivations resulting in the isolation of 13 novel cytochalasans. This study reveals that the nonproteinogenic amino acid O-methyltyrosine is the true precursor of 5, and other cryptic cytochalasans and mutasynthesis experiments produce novel halogenated pyrichalasin H analogues.
Keywords
- Cytochalasins/biosynthesis, Magnaporthe/chemistry, Molecular Structure
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic Letters, Vol. 21, No. 11, 07.06.2019, p. 4163-4167.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Targeted Gene Inactivations Expose Silent Cytochalasans in Magnaporthe grisea NI980
AU - Wang, Chongqing
AU - Hantke, Verena
AU - Cox, Russell John
AU - Skellam, Elizabeth Julia
N1 - This work was supported by the Chinese Scholarship Council [C.W. (201608310143)] and the German Research Foundation (DFG) [Grants CO 1328/2-1, INST 187/621-1, INST 187/686-1)]. The authors would also like to thank Professor Marc-Henri Lebrun (UMR BIOGER INRA AgroParisTech) and Dr. Didier Tharreau (CIRAD UMR BGPI) for the gift of the M. grisea NI980 strain and useful discussions. In addition we would like to thank Dr. Daniel Wibberg and Professor Jörn Kalinowski at CeBiTec, Bielefeld, for sequencing and annotation of M. grisea NI980. Leibniz University Hannover students Hao Xuan Zeng and Yan Cui are also thanked for assistance with extracting fungal cultures and preparing gDNA.
PY - 2019/6/7
Y1 - 2019/6/7
N2 - The biosynthetic gene cluster encoding the phytotoxin pyrichalasin H 5 was discovered in Magnaporthe grisea NI980, and the late-stage biosynthetic pathway of 5 was fully elucidated using targeted gene inactivations resulting in the isolation of 13 novel cytochalasans. This study reveals that the nonproteinogenic amino acid O-methyltyrosine is the true precursor of 5, and other cryptic cytochalasans and mutasynthesis experiments produce novel halogenated pyrichalasin H analogues.
AB - The biosynthetic gene cluster encoding the phytotoxin pyrichalasin H 5 was discovered in Magnaporthe grisea NI980, and the late-stage biosynthetic pathway of 5 was fully elucidated using targeted gene inactivations resulting in the isolation of 13 novel cytochalasans. This study reveals that the nonproteinogenic amino acid O-methyltyrosine is the true precursor of 5, and other cryptic cytochalasans and mutasynthesis experiments produce novel halogenated pyrichalasin H analogues.
KW - Cytochalasins/biosynthesis
KW - Magnaporthe/chemistry
KW - Molecular Structure
UR - http://www.scopus.com/inward/record.url?scp=85066891128&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.9b01344
DO - 10.1021/acs.orglett.9b01344
M3 - Article
C2 - 31099577
AN - SCOPUS:85066891128
VL - 21
SP - 4163
EP - 4167
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 11
ER -