Chemical Synthesis of glycoproteins having complex type oligosaccharides and elucidation of oligosaccharide functions

• Project/Area Number: 23245037
• Research Category: Grant-in-Aid for Scientific Research (A)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemistry related to living body
• Research Institution: Osaka University
• Principal Investigator: KAJIHARA Yasuhiro 大阪大学, 理学(系)研究科(研究院), 教授 (50275020)
• Project Period (FY): 2011-04-01 – 2014-03-31
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥43,810,000 (Direct Cost: ¥33,700,000、Indirect Cost: ¥10,110,000); Fiscal Year 2013: ¥8,580,000 (Direct Cost: ¥6,600,000、Indirect Cost: ¥1,980,000); Fiscal Year 2012: ¥8,580,000 (Direct Cost: ¥6,600,000、Indirect Cost: ¥1,980,000); Fiscal Year 2011: ¥26,650,000 (Direct Cost: ¥20,500,000、Indirect Cost: ¥6,150,000)
• Keywords: 糖鎖 / 糖タンパク質 / 糖ペプチド / 酵素 / チオエステル / ペプチド固相合成 / シグレック / 抗体 / ケモカイン / ペプチドチオエステル / タンパク質化学合成 / シアル酸 / Boc法 / ペプチド

Research Abstract

In order to elucidate oligosaccharide functions, chemical synthesis of homogeneous glycoprotein was examined. For the synthesis of target glycoproteins, full-length glycosylpolypeptide chains was designed to divide into several segments and these were prepared by our improved and safe tert-Boc-SPPS. Glycopeptide-alpha-thioester and peptide-alpha-thioesters thus obtained were successfully coupled by repetitive native chemical ligation. Subsequent folding experiments of chemically synthesized homogeneous glycopeptide yielded correctly folded glycoproteins with native disulfide bond patterns. Using this method, erythropoietin, chemokine and lectin were successfully synthesized.

Research Products

• [Journal Article] Safe and efficient Boc-SPPS for the synthesis of glycopeptide-α-thioesters (2014)
  • Author(s): M. Izumi, M. Murakami, R. Okamoto, Y. Kajihara
  • Journal Title: J. Pept. Sci Volume: 20 Pages: 98-101
  • Peer Reviewed
• [Journal Article] Safe and efficient Boc-SPPS for the synthesis of glycopeptide-d- thioesters (2014)
  • Author(s): Masayuki Izumi, Masumi Murakami, Ryo Okamoto and Yasuhiro
  • Journal Title: Journal of Peptide Science Volume: 20 Issue: 2 Pages: 98-101
  • DOI: 10.1002/psc.2608
  • Peer Reviewed
• [Journal Article] (Quasi-)Racemic X-ray Structures of Glycosylated and Non-Glycosylated Forms of the Chemokine Ser-CCL1 Prepared by Total Chemical Synthesis (2014)
  • Author(s): R. Okamoto, K. Mandal, M. R. Sawaya, Y. Kajihara, T.O. Yeates, S. B.H. Kent
  • Journal Title: Angew. Chem. Int. Ed Volume: - Issue: 20 Pages: 5194-5198
  • DOI: 10.1002/anie.201400679
  • Peer Reviewed
• [Journal Article] Total chemical synthesis and biological activities of glycosylated and non-glycosylated forms of the chemokines CCL1 and Ser-CCL1 (2014)
  • Author(s): R. Okamoto, K. Mandal, M. Ling, A. D. Luster, Y. Kajihara, S. B. H. Kent
  • Journal Title: Angew. Chem. Int. Ed Volume: - Issue: 20 Pages: 5188-5193
  • DOI: 10.1002/anie.201310574
  • Peer Reviewed
• [Journal Article] Misfolded glycoproteins as probes for analysis of folding sensor enzyme UDP-glucose : glycoprotein glucosyltransferase (2013)
  • Author(s): M. Izumi, T. Kiuchi, Y. Ito, Y. Kajihara
  • Journal Title: Trends in Glycoscience and Glycotechnology Volume: 25 Pages: 1-12
  • NAID: 10031190616
  • Peer Reviewed
• [Journal Article] Chemical assembly of N-glycoproteins : a refined toolbox to address a ubiquitous posttranslational modification (2013)
  • Author(s): C. Unverzagt, Y. Kajihara
  • Journal Title: Chem. Soc. Rev Volume: 42 Pages: 4408-4420
  • Peer Reviewed
• [Journal Article] Chemical assembly of N-glycoproteins: a refined toolbox to address a ubiquitous posttranslational modification (2013)
  • Author(s): C. Unverzagt, Y. Kajihara
  • Journal Title: Chem. Soc. Rev. Volume: 42 Issue: 10 Pages: 4408-4420
  • DOI: 10.1039/c3cs35485g
  • Peer Reviewed
• [Journal Article] Misfolded Glycoproteins as Probes for Analysis of Folding Sensor Enzyme UDP-Glucose (2013)
  • Author(s): Tsuboi, S.
  • Journal Title: Trends in Glycoscience and Glycotechnology Volume: 25 Issue: 141 Pages: 1-12
  • DOI: 10.4052/tigg.25.1
  • NAID: 130004841363
  • ISSN: 0915-7352, 1883-2113
  • Peer Reviewed
• [Journal Article] Chemical Synthesis of an Erythropoietin Glycoform Containing a Complex-type Disialyloligosaccharide (2012)
  • Author(s): M. Murakami, R. Okamoto, M. Izumi, Y. Kajihara
  • Journal Title: Angew. Chem. Int. Ed Volume: 51 Pages: 3567-3572
  • Peer Reviewed
• [Journal Article] A synthetic approach to a peptide alpha-thioester from unprotected peptide through cleavage and activation of a specific peptide bond by N-acetylguanidine (2012)
  • Author(s): R. Okamoto, K. Morooka, Y. Kajihara
  • Journal Title: Angew. Chem. Int. Ed Volume: 51 Pages: 191-196
  • Peer Reviewed
• [Journal Article] Homogeneous human complex type oligosaccharides in correctly folded intact glycoproteins : evaluation of the oligosaccharide influence on protein-folding, -stability, and -conformational properties (2012)
  • Author(s): Y. Kajihara, Y. Tanabe, S. Sasaoka, R. Okamoto
  • Journal Title: Chem. Eur. J Volume: 18 Pages: 5944-5953
  • Peer Reviewed
• [Journal Article] Chemical Synthesis of an Erythropoietin Glycoform Containing a Complex-type Disialyloligosaccharide (2012)
  • Author(s): M. Murakami, R. Okamoto, M. Izumi, Y. Kajihara
  • Journal Title: Angew. Chem. Int. Ed. Volume: 51 Issue: 15 Pages: 3567-3572
  • DOI: 10.1002/anie.201109034
  • Peer Reviewed
• [Journal Article] Homogeneous human complex type oligosaccharides in correctly folded intact glycoproteins: evaluation of the oligosaccharide influence on protein-folding, -stability, and -conformational properties. (2012)
  • Author(s): Y. Kajihara, Y. Tanabe, S. Sasaoka, R. Okamoto
  • Journal Title: Chem. Eur. J. Volume: 18 Issue: 19 Pages: 5944-5953
  • DOI: 10.1002/chem.201103428
  • Peer Reviewed
• [Journal Article] Chemical Synthesis of homogeneous human glycosyl-interferon-beta that exhibits potent antitumor activity in vivo (2012)
  • Author(s): I. Sakamoto, K. Tezuka, K. Fukae, K. Ishii, K. Taduru, M. Maeda, M. Ouchi, K. Yoshida, Y. Nambu, J. Igarashi, N. Hayashi, T. Tsuji, Y. Kajihara
  • Journal Title: J. Am. Chem. Soc Volume: 134 Issue: 12 Pages: 5428-5431
  • DOI: 10.1021/ja2109079
  • Peer Reviewed
• [Journal Article] Homogeneous human complex type oligosaccharides in correctly folded intact glycoproteins : evaluation of the oligosaccharide influence on protein-folding,-stability, and -conformational properties (2012)
  • Author(s): Y.Kajihara, Y.Tanabe, S.Sasaoka, R.Okamoto
  • Journal Title: Chem.Eur.J. Volume: (印刷中)
  • Peer Reviewed
• [Journal Article] A synthetic approach to a peptide alpha-thioester from unprotected peptide through cleavage and activation of a specific peptide bond by N-acetylguanidine (2012)
  • Author(s): R.Okamoto, K.Morooka, Y.Kajihara
  • Journal Title: Angew.Chem.Int.Ed Volume: 51 Issue: 1 Pages: 191-196
  • DOI: 10.1002/anie.201105601
  • Peer Reviewed
• [Journal Article] Elucidating the Function of Complex-Type Oligosaccharides by Use of Chemical Synthesis of Homogeneous Glycoproteins (2011)
  • Author(s): Y. Kajihara, M. Izumi, K. Hirano, T. Murase, D. Macmillan, R. Okamoto
  • Journal Title: Israel Journal of Chemistry Volume: 51 Pages: 917-929
  • Peer Reviewed
• [Journal Article] Elucidating the Function of Complex-type Oligosaccharide by use of Chemical Synthesis of Homogeneous Glycoproteins (2011)
  • Author(s): Y.Kajihara, M.Izumi, K.Hirano, T.Murase, D.Macmillan, R.Okamoto
  • Journal Title: Israel Journal of Chemistry Volume: 51 Issue: 8-9 Pages: 917-929
  • DOI: 10.1002/ijch.201100081
  • Peer Reviewed
• [Journal Article] Semisynthesis of erythropoietin analogue having three oligosaccharides (2011)
  • Author(s): K.Hirano, M.Izumi, D.Macmillan, K.Tezuka, T.Tsuji, Y.Kajihara
  • Journal Title: J.Carbohydr.Chem. Volume: 30 Issue: 4-6 Pages: 306-319
  • DOI: 10.1080/07328303.2011.604570
  • Peer Reviewed
• [Journal Article] Unique self-anhydride formation in the degradation of Cytidine-5'-mono-phospho-sialic acid (CMP-Neu5Ac) and Cytidine-5'-di-phospho-sialic acid (CDP-Neu5Ac) and its application CMP-sialic acid analogue synthesis (2011)
  • Author(s): Y.Kajihara, S.Nishigaki, D.Hannzawa, G.Nakanishi, R.Okamoto, N.Yamamoto
  • Journal Title: Chem.Eur.J. Volume: 17 Issue: 27 Pages: 7645-7655
  • DOI: 10.1002/chem.201003387
  • Peer Reviewed
• [Journal Article] A semisynthesis of post-translationally modified protein using chemical cleavage and activation of an expressed fusion polypeptide
  • Author(s): R.Okamoto, M. Kimura, T. Ishimizu, M. Izumi, Y. Kajihara
  • Journal Title: Chem. Eur. J Volume: (in press)
  • Peer Reviewed
• [Presentation] Chemical synthesis of misfolded and correctly folded glycoprotein (2014)
  • Author(s): Kajihara Y
  • Organizer: 27^<th> International Carbohydrate symposium
  • Place of Presentation: India, Bangalore
  • Invited
• [Presentation] Synthetic Synthesis of Homogeneous Erythropoietin Analogs Bearing a High Mannose-type Oligosaccharide and the Functional Analysis of Folding Sensor Enzyme UGGT (2014)
  • Author(s): 木内達人、岡本亮、和泉雅之、瀬古玲、伊藤幸成、梶原康宏
  • Organizer: 日本化学会第94回春季年会
  • Place of Presentation: 名古屋大学、名古屋
• [Presentation] Chemical Synthesis of Misfolded and Correctly Folded Glycoproteins: A Unique Approach for the Study of Glycoprotein Quality Control (2014)
  • Author(s): Yasuhiro Kajihara
  • Organizer: 27th International Carbohydrate symposium, India, Bangalore
  • Place of Presentation: India, Bangalore, Indian Institute of Science
  • Invited
• [Presentation] Chemical approach for the synthesis of homogeneous glycoproteins (2014)
  • Author(s): Yasuhiro Kajihara
  • Organizer: Emerging Trends in Glycoscience and glycotechnology, India
  • Place of Presentation: India, Delhi, Indian Institute of Technology
  • Invited
• [Presentation] 天然由来の二分枝アシアロ糖鎖を利用する三分枝シアリル複合型糖鎖の合成 (2013)
  • Author(s): 真木勇太、岡本亮、和泉雅之、山本岳、梶原康宏
  • Organizer: 第32回日本糖質学会年会
  • Place of Presentation: 大阪
  • Year and Date: 2013-08-05
• [Presentation] Chemical Synthesis of Homogeneous Erythropoietin bearing M9-highmannose type oligosaccharide : A Unique Approach for the Study of Glycoprotein Quality Control (2013)
  • Author(s): Kajihara Y
  • Organizer: Chemical Protein synthesis meeting
  • Place of Presentation: Vienna, Wien
• [Presentation] 均一な構造のハイマンノース型糖鎖を持つエリスロポエチンの合成 (2013)
  • Author(s): 木内達人、岡本亮、和泉雅之、伊藤幸成、梶原康宏
  • Organizer: 日本化学会第93回春季年会
  • Place of Presentation: 立命館大学、滋賀
• [Presentation] 均一な構造のハイマンノース型糖鎖を持つエリスロポエチンの合成 (2013)
  • Author(s): 木内達人、牧村裕、岡本亮、和泉雅之、瀬古玲、迫野昌文、金森審子、伊藤幸成、梶原康宏
  • Organizer: 第32回日本糖質学会年会
  • Place of Presentation: 大阪
• [Presentation] Chemical Synthesis of Homogeneous Erythropoietin bearing M9-highmannose type oligosaccharide: A Unique Approach for the Study of Glycoprotein Quality Control (2013)
  • Author(s): Yasuhiro Kajihara
  • Organizer: Chemical Protein synthesis meeting
  • Place of Presentation: Wien, Vienna, Wien university
  • Invited
• [Presentation] Chemical Synthesis of Misfolded and Correctly Folded Glycoproteins: A Unique Approach for the Study of Glycoprotein Quality Control (2013)
  • Author(s): Yasuhiro Kajihara
  • Organizer: 4th modern solid phase peptide synthesis & its application symposium
  • Place of Presentation: kobe, Miko Villa Hotel
  • Invited
• [Presentation] 均一な構造のハイマンノース型糖鎖をもつエリスロポエチンの合成 (2013)
  • Author(s): 木内達人、牧村裕、岡本亮、和泉雅之、瀬古玲、迫野昌文、金森審子、伊藤幸成
  • Organizer: 第３２回日本糖質学会年会
  • Place of Presentation: 大阪 交際交流センター
• [Presentation] 天然から単離したN-結合型糖鎖を用いる高分枝複合型糖鎖の合成研究 (2012)
  • Author(s): 真木勇太、岡本亮、和泉雅之、梶原康宏
  • Organizer: 第31回日本糖質学会年会
  • Place of Presentation: 鹿児島
  • Year and Date: 2012-09-19
• [Presentation] Chemical Synthesis of an Erythropoietin Glycoform Containing a Complex-Type Disialyloligosaccharide (2012)
  • Author(s): 村上真淑、岡本亮、和泉雅之、梶原康宏
  • Organizer: 第26回国際糖質学会
  • Place of Presentation: マドリード(スペイン)
  • Year and Date: 2012-07-25
• [Presentation] Synthetic Study of Erythropoietin Glycoforms Containing Three Complex-type Disialyloligosaccharides (2012)
  • Author(s): 村上真淑、岡本亮、和泉雅之、梶原康宏
  • Organizer: ゴードンリサーチカンファレンス
  • Place of Presentation: バーモント(アメリカ)
  • Year and Date: 2012-07-25
• [Presentation] Boc 法を利用する糖タンパク質エリスロポエチン誘導体の合成研究 (2012)
  • Author(s): 木内達人、村上真淑、岡本亮、梶原康宏
  • Organizer: 第13回関西グライコサイエンスフォーラム
  • Place of Presentation: 大阪市立大学、大阪
  • Year and Date: 2012-05-19
• [Presentation] 天然から単離したN 結合型糖鎖を用いる高分岐複合型糖鎖の合成研究 (2012)
  • Author(s): 真木勇太・岡本亮・梶原康宏
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 神奈川
  • Year and Date: 2012-03-28
• [Presentation] Homogeneous Glycoproteins : Design, Chemical Synthesis and Biological Evaluation (2012)
  • Author(s): Kajihara Y
  • Organizer: 26^<th> International Carbohydrate symposium
  • Place of Presentation: Spain, Madrid
  • Invited
• [Presentation] 新規シアリル糖ペプチドチオエステル合成法を基盤としたシアリル糖タンパク質の合成 (2012)
  • Author(s): 村上真淑、和泉雅之、岡本亮、梶原康宏
  • Organizer: 第92回日本化学会春季年会
  • Place of Presentation: 神奈川
• [Presentation] A SYNTHETIC STUDY ON ERYTHROPOIETIN GLYCOFORM CONTAINING HIGH-MANNOSE TYPE OLIGOSACCHARIDE (2012)
  • Author(s): 木内達人、岡本亮、牧村裕、和泉雅之、伊藤幸成、梶原康宏
  • Organizer: 26th International Carbohydrate Symposium
  • Place of Presentation: スペイン
• [Presentation] ハイマンノース型糖鎖を有するエリスロポエチンの合成研究 (2012)
  • Author(s): 木内達人、岡本亮、牧村裕、和泉雅之、伊藤幸成、梶原康宏
  • Organizer: 第31回日本糖質学会年会
  • Place of Presentation: 鹿児島
• [Presentation] Homogeneous Glycoproteins: Design, Chemical Synthesis and Biological Evaluation (2012)
  • Author(s): Yasuhiro Kajihara
  • Organizer: 26th International Carbohydrate symposium
  • Place of Presentation: Madrid, Spain, Melia Castilla Madrid Hotel
  • Invited
• [Presentation] 糖タンパク質の精密化学合成と糖鎖機能解明 (2012)
  • Author(s): 梶原康宏
  • Organizer: 第１２回日本蛋白質科学会年会
  • Place of Presentation: 名古屋 国際会議場
  • Invited
• [Presentation] Chemical Synthesis of Homogeneous Erythropoietin bearing M9-highmannose type oligosaccharide: A Unique Approach for the Study of Glycoprotein Quality Control, Chemical Protein synthesis meeting (2012)
  • Author(s): Yasuhiro Kajihara
  • Organizer: Chemical Protein synthesis meeting
  • Place of Presentation: Vienna, Wien, Wien university
  • Invited
• [Presentation] エリスロポエチンの化学合成を基盤とする糖鎖機能解明の研究 (2012)
  • Author(s): 岡本亮、村上真淑、和泉雅之、梶原康宏
  • Organizer: 第３１回日本糖質学会年会
  • Place of Presentation: 鹿児島、鹿児島市民文化ホール
• [Presentation] フォールディングセンサーUGGTによる合成変性糖タンパク質の基質認識 (2012)
  • Author(s): 和泉雅之、牧村裕、Simone Dedola、瀬古玲、金森審子、伊藤幸成、梶原康宏
  • Organizer: 第３１回日本糖質学会年会
  • Place of Presentation: 鹿児島、鹿児島市民文化ホール
• [Presentation] 新規シアリル糖ペプチドチオエステル合成法を基盤としたシアリル糖タンパク質の合成 (2012)
  • Author(s): 村上真淑、和泉雅之、岡本亮、梶原康宏
  • Organizer: 第92回日本化学会春季年会
  • Place of Presentation: 慶應大学(神奈川)
• [Presentation] ペプチドグアニジン誘導体を鍵化合物とした新規なタンパク質化学合成法の開発 (2012)
  • Author(s): 岡本亮、梶原康宏
  • Organizer: 第92回日本化学会春季年会
  • Place of Presentation: 慶應大学(神奈川)
• [Presentation] 天然から単離したN結合型糖鎖を用いる高分岐複合型糖鎖の合成研究 (2012)
  • Author(s): 真木勇太、岡本亮、梶原康宏
  • Organizer: 第92回日本化学会春季年会
  • Place of Presentation: 慶應大学(神奈川)
• [Presentation] Uncovering a Reason Why Sialoside is Labile and Its Application for the Synthesis of Homogeneous Glycoproteins (2011)
  • Author(s): Kajihara, Y, Murakami, M., Okamoto R
  • Organizer: Asian Communications of Glycobiology and glycotechno logy 3nd Conference.
  • Place of Presentation: 上海有機化学研究所(Shanghai, China)
  • Year and Date: 2011-10-27
• [Presentation] Boc 固相合成法を用いたヒト複合型シアリル糖鎖を持つ糖ペプチドチオエステルの新規合成法 (2011)
  • Author(s): 村上真淑、岡本亮、梶原康宏
  • Organizer: 第12回関西グライコサイエンスフォーラム
  • Place of Presentation: 大阪
  • Year and Date: 2011-05-14
• [Presentation] Boc固相合成法を用いたヒト複合型シアリル糖鎖を持つ糖ペプチドチオエステルの新規合成法 (2011)
  • Author(s): 村上真淑、岡本亮、梶原康宏
  • Organizer: 第12回関西グライコサイエンスフォーラム
  • Place of Presentation: 大阪大学(大阪)
  • Year and Date: 2011-05-14
• [Presentation] Boc 固相合成法を用いたシアリル糖ペプチドチオエステル体の新規調製法 (2011)
  • Author(s): 村上真淑、岡本亮、梶原康宏
  • Organizer: 第30回日本糖質学会年会
  • Place of Presentation: 新潟
• [Presentation] Boc固相合成法を用いたシアリル糖ペプチドチオエステル体の新規調製法 (2011)
  • Author(s): 村上真淑、岡本亮、梶原康宏
  • Organizer: 第30回日本糖質学会年会
  • Place of Presentation: 長岡リリックホール(新潟)
• [Presentation] 卵黄由来ハイマンノース型糖鎖とBoc法を用いた糖ペプチドチオエステルの効率的合成 (2011)
  • Author(s): 牧村裕、木内達人、和泉雅之、Dedola Simone、伊藤幸成、梶原康宏
  • Organizer: 第30回日本糖質学会年会
  • Place of Presentation: 長岡リリックホール(新潟)
• [Presentation] N-アセチルグアニジンを脱離基とした新規な速度論的ライゲーション反応の開発とAILIM/ICOSの合成への利用 (2011)
  • Author(s): 中町圭佑、岡本亮、梶原康宏
  • Organizer: 第48回ペプチド討論会
  • Place of Presentation: 札幌コンベンションセンター(北海道)
• [Presentation] Efficient and practical synthetic methods of glycopeptide-^αthioesters (2011)
  • Author(s): Kajihara, Y., Murakami, M.Izumi, M., Morooka, K., Okamoto, R.
  • Organizer: 16^<th> European Carbohydrate Symposium
  • Place of Presentation: Hilton Sorrento (Sorrento, Italy)
• [Presentation] Approaches for elucidation of oligosaccharide functions using the chemically synthesized homogeneous glycoproteins (2011)
  • Author(s): Kajihara Y
  • Organizer: 糖鎖科学日蘭共同セミナー2011
  • Place of Presentation: 名古屋大学医学部(愛知)(招待講演)
• [Presentation] Total Chemical Synthesis of a Glycosyl Chemokine : Ser-CCL1 and Structural Analysis by Quasi-Racemate X-ray Crystallography (2011)
  • Author(s): Ryo Okamoto, Kalyaneswar Mandal, Michael Sawaya, Yasuhiro Kajihara, Todd O.Yeates, Stephen B.H.Kent
  • Organizer: 22nd American Peptide Symposium
  • Place of Presentation: Sheraton SanDiego (SanDiego, USA)
• [Book] Glycochemical Synthesis: Strategies and Applications (2014)
  • Author(s): Yasuhiro Kajihara, Masumi Murakami and Carlo Unverzagt
  • Publisher: Wiley-Blackwell
• [Book] 化学 (2013)
  • Author(s): 村上真淑、岡本亮、和泉雅之、梶原康宏
  • Publisher: 化学同人
• [Book] 最新ペプチド合成技術とその創薬研究への応用 (2012)
  • Author(s): 岡本亮、梶原康宏
  • Publisher: メディカルドウ
• [Book] The Momentum of Chemical Glycoprotein Synthesis
  • Author(s): Yasuhiro Kajihara, Masumi Murakami and Carlo Unverzagt
  • Publisher: Wiley (印刷中)
• [Patent(Industrial Property Rights)] NCL 法に適した、ポリペプチド断片の効率的な製造方法 (2014)
  • Inventor(s): 梶原康宏、岡本亮、木村元春、石井一之
  • Industrial Property Rights Holder: 糖鎖工学研究所(株)
  • Industrial Property Rights Type: 特許
  • Filing Date: 2014-03-25
  • Overseas
• [Patent(Industrial Property Rights)] アリル糖鎖を有する糖ペプチドの製造方法、当該製造方法に使用するシアリル糖鎖付加アミノ酸誘導体、及び当該糖ペプチド (2013)
  • Inventor(s): 梶原康宏、村上真淑、石井一之
  • Industrial Property Rights Holder: 糖鎖工学研究所(株)
  • Industrial Property Rights Type: 特許
  • Filing Date: 2013-09-06
  • Overseas
• [Patent(Industrial Property Rights)] 糖ペプチドチオエステルの調整法 (2012)
  • Inventor(s): 梶原康宏, 村上真淑, 石井一之
  • Industrial Property Rights Holder: 大阪大学,大塚化学
  • Industrial Property Number: 2012-021367
  • Filing Date: 2012-02-02