Expanding the Structural Diversity of Polyketides by Exploring the Cofactor Tolerance of an Inline Methyltransferase Domain

Winter, Jaclyn M.; Chiou, Grace; Bothwell, Ian R.; Xu, Wei; Garg, Neil K.; Luo, Minkui; Tang, Yi

doi:10.1021/ol401723h

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Expanding the Structural Diversity of Polyketides by Exploring the Cofactor Tolerance of an Inline Methyltransferase Domain

7 19 2013
By Winter, Jaclyn M. ; Chiou, Grace ; Bothwell, Ian R. ; ...
http://dx.doi.org/10.1021/ol401723h
Source: Org Lett. 15(14):3774-3777

[PDF-748.64 KB]

English

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Details:

Alternative Title:

Org Lett
Personal Author:

Winter, Jaclyn M. ; Chiou, Grace ; Bothwell, Ian R. ; Xu, Wei ; Garg, Neil K. ; ... More +

Winter, Jaclyn M. ; Chiou, Grace ; Bothwell, Ian R. ; Xu, Wei ; Garg, Neil K. ; Luo, Minkui ; Tang, Yi Less -
Description:

A strategy for introducing structural diversity into polyketides by exploiting the promiscuity of an in-line methyltransferase domain in a multidomain polyketide synthase is reported. In vitro investigations using the highly-reducing fungal polyketide synthase CazF revealed that its methyltransferase domain accepts the nonnatural cofactor propargylic Se-adenosyl-l-methionine and can transfer the propargyl moiety onto its growing polyketide chain. This propargylated polyketide product can then be further chain-extended and cyclized to form propargyl-α pyrone or be processed fully into the alkyne-containing 4'-propargyl-chaetoviridin A.
Subjects:

[+]

Amino Acid Sequence Furans Methyltransferases Pargyline Polyketides Polyketide Synthases Protein Structure, Tertiary Pyrones
Source:

Org Lett. 15(14):3774-3777
Pubmed ID:

23837609
Pubmed Central ID:

PMC3779521
Document Type:

Journal Article
Funding:

R01 GM096056/GM/NIGMS NIH HHSUnited States/ ; DP1 GM106413/GM/NIGMS NIH HHSUnited States/ ; DP2 OD007335/OD/NIH HHSUnited States/ ; T32 GM008496/GM/NIGMS NIH HHSUnited States/ ; S10 RR025631/RR/NCRR NIH HHSUnited States/ ; ... More +

R01 GM096056/GM/NIGMS NIH HHSUnited States/ ; DP1 GM106413/GM/NIGMS NIH HHSUnited States/ ; DP2 OD007335/OD/NIH HHSUnited States/ ; T32 GM008496/GM/NIGMS NIH HHSUnited States/ ; S10 RR025631/RR/NCRR NIH HHSUnited States/ ; S10RR025631/RR/NCRR NIH HHSUnited States/ ; 1DP2OD007335/OD/NIH HHSUnited States/ ; 1DP1GM106413/DP/NCCDPHP CDC HHSUnited States/ ; 1R01GM096056/GM/NIGMS NIH HHSUnited States/ Less -
Volume:

15
Issue:

14
Collection(s):

CDC Public Access
Main Document Checksum:

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urn:sha256:95d0adf5be7d16056dc563d45523f04a3ad571b1704f70ea7e839f54fe44bea3
Download URL:

https://stacks.cdc.gov/view/cdc/29741/cdc_29741_DS1.pdf
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