132. Narita K, Sato H, Minami A, Kudo K, Gao L, Liu C, Ozaki T, Kodama M, Lei X, Taniguchi T,
Monde K, Yamazaki M, Uchiyama M, Oikawa H (2017) Focused genome mining of structurally related sesterterpenes: enzymatic formation of enantiomeric and diastereomeric products. Org Lett 19:6696
133. Ye Y, Minami A, Mandi A, Liu C, Taniguchi T, Kuzuyama T, Monde K, Gomi K, Oikawa H
(2015) Genome mining for sesterterpenes using bifunctional terpene synthases reveals a
unified intermediate of di/sesterterpenes. J Am Chem Soc 137:11846
134. Sato H, Narita K, Minami A, Yamazaki M, Wang C, Suemune H, Nagano S, Tomita T,
Oikawa H, Uchiyama M (2018) Theoretical study of sesterfisherol biosynthesis: computational prediction of key amino acid residue in terpene synthase. Sci Rep 8:2473
135. Shao J, Chen QW, Lv HJ, He J, Liu ZF, Lu YN, Liu HL, Wang GD, Wang Y (2017) (+)Thalianatriene and (–)-retigeranin B catalyzed by sesterterpene synthases from Arabidopsis
thaliana. Org Lett 19:1816
136. Huang AC, Hong YJ, Bond AD, Tantillo DJ, Osbourn A (2018) Diverged plant terpene
synthases reroute the carbocation cyclization path towards the formation of unprecedented
6/11/5 and 6/6/7/5 sesterterpene scaffolds. Angew Chem Int Ed 57:1291
137. Rinkel J, Lauterbach L, Dickschat JS (2017) Spata-13,17-diene synthase — an enzyme with
sesqui-, di-, and sesterterpene synthase activity from Streptomyces xinghaiensis. Angew Chem
Int Ed 56:16385
138. Matsuda Y, Mitsuhashi T, Lee S, Hoshino M, Mori T, Okada M, Zhang H, Hayashi F,
Fujita M, Abe I (2016) Astellifadiene: structure determination by NMR spectroscopy and
crystalline sponge method, and elucidation of its biosynthesis. Angew Chem Int Ed 55:5785
139. Sato T, Yamaga H, Kashima S, Murata Y, Shinada T, Nakano C, Hoshino T (2013) Identification of novel sesterterpene/triterpene synthase from Bacillus clausii. Chembiochem 14:822
140. Yang Y, Zhang Y, Zhang S, Chen Q, Ma K, Bao L, Tao Y, Yin W, Wang G, Liu H (2018)
Identification and characterization of a membrane-bound sesterterpene cyclase from Streptomyces somaliensis. J Nat Prod 81:1089
141. Chen M, Chou WK, Toyomasu T, Cane DE, Christianson DW (2016) Structure and function of
fusicoccadiene synthase, a hexameric bifunctional diterpene synthase. ACS Chem Biol 11:889
142. Chen M, Harris GG, Pemberton TA, Christianson DW (2016) Multi-domain terpenoid cyclase
architecture and prospects for proximity in bifunctional catalysis. Curr Opin Struct Biol 41:27
143. Qin B, Matsuda Y, Mori T, Okada M, Quan Z, Mitsuhashi T, Wakimoto T, Abe I (2016) An
unusual chimeric diterpene synthase from Emericella variecolor and its functional conversion
into a sesterterpene synthase by domain swapping. Angew Chem Int Ed 55:1658
144. Pemberton TA, Chen M, Harris GG, Chou WK, Duan L, Köksal M, Genshaft AS, Cane DE,
Christianson DW (2017) Exploring the influence of domain architecture on the catalytic
function of diterpene synthases. Biochemistry 56:2010
145. Huang JH, Lv JM, Wang QZ, Zou J, Lu YJ, Wang QL, Chen DN, Yao XS, Gao H, Hu D
(2019) Biosynthesis of an anti-tuberculosis sesterterpenoid asperterpenoid A. Org Biomol
Chem 17:248
146. Gao L, Narita K, Ozaki T, Kumakura N, Gan P, Minami A, Liu C, Lei X, Shirasu K, Oikawa H
(2018) Identification of novel sesterterpenes by genome mining of phytopathogenic fungi
Phoma and Colletotrichum sp. Tetrahedron Lett 59:1136
147. Matsuda Y, Mitsuhashi T, Quan Z, Abe I (2015) Molecular basis for stellatic acid biosynthesis: a genome mining approach for discovery of sesterterpene synthases. Org Lett 17:4644
148. Chiba R, Minami A, Gomi K, Oikawa H (2013) Identification of ophiobolin F synthase by a
genome mining approach: a sesterterpene synthase from Aspergillus clavatus. Org Lett 5:594
149. Chai H, Yin R, Liu Y, Meng H, Zhou X, Zhou G, Bi X, Yang X, Zhu T, Zhu W, Deng Z, Hong
K (2016) Sesterterpene ophiobolin biosynthesis involving multiple gene clusters in Aspergillus ustus. Sci Rep 6:27181
150. Yan J, Guo J, Yuan W, Mai W, Hong K (2018) Identification of enzymes involved in
sesterterpene biosynthesis in marine fungi. Methods Enzymol 604:441
151. Yuan W, Lv S, Chen L, Zhao Y, Deng Z, Hong K (2019) Production of sesterterpene
ophiobolin by a bifunctional terpene synthase in Escherichia coli. Appl Microbiol Biotechnol
103:8785
Sesterterpenoids
77
Monde K, Yamazaki M, Uchiyama M, Oikawa H (2017) Focused genome mining of structurally related sesterterpenes: enzymatic formation of enantiomeric and diastereomeric products. Org Lett 19:6696
133. Ye Y, Minami A, Mandi A, Liu C, Taniguchi T, Kuzuyama T, Monde K, Gomi K, Oikawa H
(2015) Genome mining for sesterterpenes using bifunctional terpene synthases reveals a
unified intermediate of di/sesterterpenes. J Am Chem Soc 137:11846
134. Sato H, Narita K, Minami A, Yamazaki M, Wang C, Suemune H, Nagano S, Tomita T,
Oikawa H, Uchiyama M (2018) Theoretical study of sesterfisherol biosynthesis: computational prediction of key amino acid residue in terpene synthase. Sci Rep 8:2473
135. Shao J, Chen QW, Lv HJ, He J, Liu ZF, Lu YN, Liu HL, Wang GD, Wang Y (2017) (+)Thalianatriene and (–)-retigeranin B catalyzed by sesterterpene synthases from Arabidopsis
thaliana. Org Lett 19:1816
136. Huang AC, Hong YJ, Bond AD, Tantillo DJ, Osbourn A (2018) Diverged plant terpene
synthases reroute the carbocation cyclization path towards the formation of unprecedented
6/11/5 and 6/6/7/5 sesterterpene scaffolds. Angew Chem Int Ed 57:1291
137. Rinkel J, Lauterbach L, Dickschat JS (2017) Spata-13,17-diene synthase — an enzyme with
sesqui-, di-, and sesterterpene synthase activity from Streptomyces xinghaiensis. Angew Chem
Int Ed 56:16385
138. Matsuda Y, Mitsuhashi T, Lee S, Hoshino M, Mori T, Okada M, Zhang H, Hayashi F,
Fujita M, Abe I (2016) Astellifadiene: structure determination by NMR spectroscopy and
crystalline sponge method, and elucidation of its biosynthesis. Angew Chem Int Ed 55:5785
139. Sato T, Yamaga H, Kashima S, Murata Y, Shinada T, Nakano C, Hoshino T (2013) Identification of novel sesterterpene/triterpene synthase from Bacillus clausii. Chembiochem 14:822
140. Yang Y, Zhang Y, Zhang S, Chen Q, Ma K, Bao L, Tao Y, Yin W, Wang G, Liu H (2018)
Identification and characterization of a membrane-bound sesterterpene cyclase from Streptomyces somaliensis. J Nat Prod 81:1089
141. Chen M, Chou WK, Toyomasu T, Cane DE, Christianson DW (2016) Structure and function of
fusicoccadiene synthase, a hexameric bifunctional diterpene synthase. ACS Chem Biol 11:889
142. Chen M, Harris GG, Pemberton TA, Christianson DW (2016) Multi-domain terpenoid cyclase
architecture and prospects for proximity in bifunctional catalysis. Curr Opin Struct Biol 41:27
143. Qin B, Matsuda Y, Mori T, Okada M, Quan Z, Mitsuhashi T, Wakimoto T, Abe I (2016) An
unusual chimeric diterpene synthase from Emericella variecolor and its functional conversion
into a sesterterpene synthase by domain swapping. Angew Chem Int Ed 55:1658
144. Pemberton TA, Chen M, Harris GG, Chou WK, Duan L, Köksal M, Genshaft AS, Cane DE,
Christianson DW (2017) Exploring the influence of domain architecture on the catalytic
function of diterpene synthases. Biochemistry 56:2010
145. Huang JH, Lv JM, Wang QZ, Zou J, Lu YJ, Wang QL, Chen DN, Yao XS, Gao H, Hu D
(2019) Biosynthesis of an anti-tuberculosis sesterterpenoid asperterpenoid A. Org Biomol
Chem 17:248
146. Gao L, Narita K, Ozaki T, Kumakura N, Gan P, Minami A, Liu C, Lei X, Shirasu K, Oikawa H
(2018) Identification of novel sesterterpenes by genome mining of phytopathogenic fungi
Phoma and Colletotrichum sp. Tetrahedron Lett 59:1136
147. Matsuda Y, Mitsuhashi T, Quan Z, Abe I (2015) Molecular basis for stellatic acid biosynthesis: a genome mining approach for discovery of sesterterpene synthases. Org Lett 17:4644
148. Chiba R, Minami A, Gomi K, Oikawa H (2013) Identification of ophiobolin F synthase by a
genome mining approach: a sesterterpene synthase from Aspergillus clavatus. Org Lett 5:594
149. Chai H, Yin R, Liu Y, Meng H, Zhou X, Zhou G, Bi X, Yang X, Zhu T, Zhu W, Deng Z, Hong
K (2016) Sesterterpene ophiobolin biosynthesis involving multiple gene clusters in Aspergillus ustus. Sci Rep 6:27181
150. Yan J, Guo J, Yuan W, Mai W, Hong K (2018) Identification of enzymes involved in
sesterterpene biosynthesis in marine fungi. Methods Enzymol 604:441
151. Yuan W, Lv S, Chen L, Zhao Y, Deng Z, Hong K (2019) Production of sesterterpene
ophiobolin by a bifunctional terpene synthase in Escherichia coli. Appl Microbiol Biotechnol
103:8785
Sesterterpenoids
77