Presentations -

The development of the synthetic routes utilizing the selectivity in enzyme catalysis

T. Sugai

Pacificem2021 (Online) , 

2021.12

, 

Oral presentation (invited, special), Pacifichem

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In the organic process chemistries, the integrated use of
chemo- (organic synthesis) enzymatic (biotechnology) transformation
approach takes advantages over individual procedures, towards the best
solution to make the design and diagram for target compounds. In this talk,
we focus upon the use of lipases, which are developed for food
manufacturing and detergent industries, and cheaply commercially
available. Lipases work starting by the nucleophilic attack of serine hydroxy
groups involved in their active sites, and the subsequent decomposition of
enzyme-substrate complexes provide products and regenerate active
enzymes. By the attack with alcohols for the latter step, lipases, especially
in immobilized forms, exhibit the catalytic activities of transesterification in
organic solvents. Those activities were demonstrated for deprotection of
phenolic esters and kinetic resolution of enantiomers [1]. The rate of lipasecatalyzed
transesterification on polyphenolic substrates are affected by the
neighboring steric hindrance [2]. When flavonoid acetates and their
glycosylated forms were submitted to lipase-catalyzed transestericiation
conditions, deacetylation preferentially occur at C-4‘ position, the least
hindered phenolic acetates [3-5]. When severely hindered
naphthohydroquinone diacetate with both ortho- and peri- substituents,
diverse site selectivity was observed depending upon the sort of lipases [6].
Lipase-triggered aldol reaction is also presented. Indoxyl acetate was a
good substrate for the deacetylation with lipases. The syntheses of
indirubin and 6-bromoindirubin were achieved via the aldol condensation
between isatins and an indoxyl anion generated by lipase-catalyzed
reaction with triethylamine, under anhydrous and anaerobic conditions as
the key step [7]

Enzyme-assisted syntheses of bioactive compounds, originated from Scripps days

T. Sugai

2019 Scripps Korea Society Symposium (Yonsei University, Seoul, Korea) , 

2019.08

, 

Oral presentation (invited, special)

New Entries for Transformation of Carbohydrates towards the Synthesis of Bioactive Compounds

T. Sugai

2018 Frontiers in Chemical Biology (Hotel Royal Chiao Hsi, Yilan County, Taiwan) , 

2018.08

, 

Oral presentation (invited, special)

Enzyme-catalyzed Asymmetric Reduction of Cyclic Ketoesters and Application to Natural Product Synthesis

T. Sugai, K. Kuwata, R. Tsunekawa, R. Fujita

The 13th Yonsei CBMH-Keio LCC Joint Symposium (Yonsei University, Seoul, Korea) , 

2017.10

, 

Oral presentation (invited, special)

The Complementary and Integrated Chemo-enzymatic Processes for Fine Chemical Syntheses (Invited Lecture)

T. Sugai, Y. Yamashita, Y. Niitsu, M. Hamada, C. Hiraoka, T. Higashi, M. Shoji

The 14th Asia Pacific Confederation of Chemical Engineering (Singapore, Singapore) , 

2012.02

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Oral presentation (invited, special)

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カルバ糖およびDHMEQを題材に、リパーゼによる位置および立体選択的変換について最新の成果を報告した。

Chemo-enzymatic approaches towards both enatiomers of dehydroxymethylepoxy-quinomicin (DHMEQ) (Selected Oral Presentation)

T. Sugai, C. Hiraoka, M. Hamada, Y. Niitsu, R. Kobayashi, K. Nakagawara, T. Seki, M. Suzuki, Y. Yamashita, T. Higashi, M. Shoji, K. Umezawa

10th International Symposium on Biocatalysis and Biotransformations (Giardini Naxos, Italy) , 

2011.10

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Oral presentation (general)

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DHMEQを題材に、リパーゼによる位置および立体選択的変換について最新の成果を報告した。

Regio- and stereoselective lipase-catalyzed reactions on sugars and carbasugars (Invited Lecture)

M. Hamada, Y. Ueda, N. Chishima, J. Calveras, T. Higashi, M. Shoji, T. Sugai

The International Chemical Congress of Pacific Basin Societies (Honolulu, Hawaii) , 

2010.12

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Oral presentation (invited, special)

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glucal誘導体およびカルバ糖、さらにはDHMEQを題材に、リパーゼによる位置および立体選択的変換について最新の成果を報告した。

Recognition of Remote Chiral Centers in the Course of Lipase-Catalyzed Resolution and Its Application to Both Enantiomers of TBMB Acid (Invited Lecture)

T. Sugai

BIT's Inaugural Symposium on Enzymes & Biocatalysis (Shanghai, China) , 

2010.04

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Oral presentation (invited, special)

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TBMBカルボン酸を題材に、リパーゼによる遠隔不斉中心立体認識、微生物不斉還元と化学合成を組み合わせる手法について概説した。

Towards the bioactive substances based on B. subtilis epoxide hydrolase-catalyzed kinetic resolution (Invited Lecture)

T. Sugai

4th KEIO LCC - Yonsei CBMH Joint Symposium 2008 (慶應義塾大学) , 

2008.09

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Oral presentation (invited, special)

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エポキシドヒドロラーゼを基盤とするラセミ体エポキシドの光学分割、ニトリルヒドラターゼやリパーゼと組み合わせた、生物活性物質合成への展開について紹介した。

The synthesis of (R)-bicalutamide based on B. subtilis epoxide hydrolase-catalyzed kinetic resolution (Invited Lecture)

A. Fujino, M. Asano, T. Sugai

KEIO LCC - Yonsei CBMH Joint Symposium 2007 (Yonsei University, Korea) , 

2007.11

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Poster presentation

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エポキシドヒドロラーゼを用いたラセミ体エポキシドの光学分割、および生物活性物質合成への展開について紹介した。

Lithium-ethylenediamine-THF Reduction System with High Electron Transfer Ability (Short Invited Lecture)

T. Sugai, T. Shindo, Y. Fukuyama, T. Takanami, M. Matsuda, R. Obata, S. Nishiyama

2nd International Symposium on Organic Electron Transfer Chemistry (ISOETC-2007) (慶應義塾大学（横浜）) , 

2007.07

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Oral presentation (invited, special)

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溶解金属還元の新しい強力な手法を見出し、芳香族エーテルの脱メチル化、脱ベンジル化、三重結合の還元や脱スルホン化などに応用した。

Contribution to Fundamental Glycochemistry, Based on the Development of New and Unusual Transformations of Naturally Abundant Carbohydrates (Invited Lecture)

T. Sugai

21st Century COE KEIO-LCC International Symposium on Organic and Bioorganic Chemistry (慶應義塾大学（横浜）) , 

2005.11

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Oral presentation (invited, special)

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酵素法、新規に見出したケトエステル合成法、ピラノース－フラノース転位反応などを基盤とする、希少糖およびヌクレオシド類の合成研究について紹介した。

New, Unexpected Pyranose-furanose Rearrangement towards the Synthetic Studies on Rare Sugars and Nucleoside (Invited Lecture)

T. Sugai

The 15th International Symposium on Fine Chemistry and Functional Polyer (FCFPXV-2005 (Shanghai, China) , 

2005.10

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Oral presentation (invited, special)

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新しいピラノース－フラノース転位反応を基盤とする、希少糖およびヌクレオシド類の合成研究について紹介した。

Complementary Use of Chemo-enzymatic Reactions in the New Synthesis of Chiral, Non-racemic Molecules (Invited Lecture)

T. Sugai

The 14th International Symposium on Fine Chemistry and Functional Polyer (FCFPXIV-2004) (Hohhot, China) , 

2004.08

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Oral presentation (invited, special)

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微生物酵素の特性を活かした官能基変換・光学活性体調製を化学法と相補的、相乗的に組み合わせ有用物質を合成した著者らの成果、特に酵母還元を鍵段階とする新規物質創製について講演した。

Complementary and Synergistic Application of Enzyme and Molecular Catalysis (Plenary/Invited Lecture)

T. Sugai

6th International Symposium on Biocatalysis and Biotransformation - Biotrans' 03 (Oromouz, Czech Republic) , 

2003.06

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Oral presentation (invited, special)

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微生物酵素の特性を活かした官能基変換・光学活性体調製を化学法と相補的、相乗的に組み合わせ有用物質を合成した著者らの総合的な成果について講演した。

Chemo-enzymatic Synthesis toward Oligosaccharides (invited Lecture)

T. Sugai

Workshop for Junior Chemists, National Science Council Program of Taiwan (Institute of Chemistry, Academia Sinica), 

2002.11

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Oral presentation (invited, special)

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酵素微生物を活用する、糖質関連化合物の合成研究について講演した。

Integrated and Complementary Use of Chemical and Enzymatic Transformation (Invited Lecture)

T. Sugai

Workshop for Junior Chemists, National Science Council Program of Taiwan (National Tsing Hua University) (National Tsing Hua University) , 

2002.11

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Oral presentation (invited, special)

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微生物不斉還元、酵素光学分割と化学的な炭素－炭素結合形成、官能基変換を組み合わせた有用物質合成について講演した。

Synthesis of Pure Enantiomers by means of Enzyme-catalyzed Reaction (Invited Lecture)

T. Sugai

Workshop for Junior Chemists, National Science Council Program of Taiwan (National Taiwan University), 

2002.11

, 

Oral presentation (invited, special)

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酵素による鏡像体分割、微生物不斉還元などを鍵段階とする、光学活性物質の合成法に関する最新の知見について講演した。

Enzyme-catalyzed Synthesis of Aminosugars (Invited Lecture)

T. Sugai

Riken Forum on the Frontier Science Program of Glycotechnology (International) (理化学研究所) , 

1995.10

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Oral presentation (invited, special)

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標題のトピックについて、著者らの最新の成果を報告した。

Enzyme in Organic Synthesis: Use of Sialic Acid Aldolase and Pyruvate Decarboxylase (Invited Paper)

T.Sugai，S.Hiramatsu，A.Kuboki，H.Okazaki，K.Suzuki，H.Ohta

Annual Meeting of American Chemical Society, Sympsoium on Biocatalysis for Production of Non-Protein Speciality Chemicals, 

1995.04

, 

Oral presentation (invited, special)

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ピルビン酸脱炭酸酵素をキーワードとして、シアル酸など糖質の効率的合成、光学活性ジオール類の合成を達成した。