Title:
NOVEL OLIGOSACCHARIDE, PRODUCTION INTERMEDIATE FOR NOVEL OLIGOSACCHARIDE, PRODUCTION METHOD FOR NOVEL OLIGOSACCHARIDE, AND PRODUCTION METHOD FOR PRODUCTION INTERMEDIATE FOR NOVEL OLIGOSACCHARIDE
Document Type and Number:
WIPO Patent Application WO/2024/053574
Kind Code:
A1
Abstract:
[Problem] The present invention addresses the problem of providing a novel oligosaccharide that is a two-branched glycan that has an α2,6-sialic acid structure at the non-reducing end, a production method for the oligosaccharide, an intermediate for the oligosaccharide, and a production method for the intermediate. [Solution] Provided are a novel oligosaccharide represented by formula A-22, a production method for the oligosaccharide as shown in fig. 1, an intermediate for the oligosaccharide, and a production method for the intermediate.
More Like This:
Inventors:
UEDA TSUYOSHI (JP)
ITOH RYUSEI (JP)
NAKAMURA TATSUYA (JP)
ITOH RYUSEI (JP)
NAKAMURA TATSUYA (JP)
Application Number:
PCT/JP2023/032064
Publication Date:
March 14, 2024
Filing Date:
September 01, 2023
Export Citation:
Assignee:
DAIICHI SANKYO CO LTD (JP)
International Classes:
C07H1/00; C07H3/06; C07H15/203; C08B37/00
Domestic Patent References:
| WO2016076440A1 | 2016-05-19 | |||
| WO2014115797A1 | 2014-07-31 | |||
| WO2015080603A1 | 2015-06-04 | |||
| WO2022191313A1 | 2022-09-15 | |||
| WO2023074843A1 | 2023-05-04 |
Foreign References:
| JP2019515876A | 2019-06-13 | |||
| US20120226024A1 | 2012-09-06 | |||
| JP2009155353A | 2009-07-16 | |||
| JP2018021001A | 2018-02-08 | |||
| US20140051603A1 | 2014-02-20 |
Other References:
LI WEI, GAO YU, LI QING, LI ZHONG-JUN: "Ionic-liquid supported rapid synthesis of an N -glycan core pentasaccharide on a 10 g scale", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 16, no. 25, 27 June 2018 (2018-06-27), pages 4720 - 4727, XP055966256, ISSN: 1477-0520, DOI: 10.1039/C8OB01046C
MITSUHIRO IWAMOTO, TAKAHIRO YAMAGUCHI, YUKIKO SEKIGUCHI, SHOHEI OISHI, TAKESHI SHIIKI, MASAKO SOMA, KENSUKE NAKAMURA, MAKOTO YOSHI: "Pharmacokinetic and Pharmacodynamic Profiles of Glyco-Modified Atrial Natriuretic Peptide Derivatives Synthesized Using Chemo-enzymatic Synthesis Approaches", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 29, no. 8, 15 August 2018 (2018-08-15), US , pages 2829 - 2837, XP055641868, ISSN: 1043-1802, DOI: 10.1021/acs.bioconjchem.8b00427
SHIVATARE SACHIN S.; CHANG SHIH-HUANG; TSAI TSUNG-I; TSENG SUSAN YU; SHIVATARE VIDYA S.; LIN YIH-SHYAN; CHENG YANG-YU; REN CHIEN-T: "Modular synthesis of-glycans and arrays for the hetero-ligand binding analysis of HIV antibodies", NATURE CHEMISTRY, NATURE PUBLISHING GROUP UK, LONDON, vol. 8, no. 4, 7 March 2016 (2016-03-07), London, pages 338 - 346, XP037134772, ISSN: 1755-4330, DOI: 10.1038/nchem.2463
LI LEI, LIU YUNPENG, MA CHENG, QU JINGYAO, CALDERON ANGIE D., WU BAOLIN, WEI NA, WANG XUAN, GUO YUXI, XIAO ZHONGYING, SONG JING, S: "Efficient chemoenzymatic synthesis of an N-glycan isomer library", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 6, no. 10, 14 September 2015 (2015-09-14), United Kingdom , pages 5652 - 5661, XP093146918, ISSN: 2041-6520, DOI: 10.1039/C5SC02025E
NAKAHARA, Y. SHIBAYAMA, S. NAKAHARA, Y. OGAWA, T.: "Rationally designed syntheses of high-mannose and complex type undecasaccharides", CARBOHYDRATE RESEARCH, PERGAMON, GB, vol. 280, no. 1, 4 January 1996 (1996-01-04), GB , pages 67 - 84, XP004018834, ISSN: 0008-6215, DOI: 10.1016/0008-6215(95)00262-6
TAKATANI M, NAKAMA T, KUBO K, MANABE S, NAKAHARA Y, ITO Y: "Synthesis of N-linked pentasaccharides with isomeric glycosidic linkage", GLYCOCONJUGATE JOURNAL, CHAPMAN & HALL, BOSTON, vol. 17, no. 6, 1 June 2000 (2000-06-01), Boston , pages 361 - 375, XP093146922, ISSN: 0282-0080, DOI: 10.1023/A:1007151913476
FAIRBANKS ANTONY J: "Synthetic and semi-synthetic approaches to unprotected N -glycan oxazolines", BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 14, 1 January 2018 (2018-01-01), pages 416 - 429, XP055966254, DOI: 10.3762/bjoc.14.30
SACHIN S. SHIVATARE, LIN-YA HUANG, YI-FANG ZENG, JUNG-YU LIAO, TSAI-HONG YOU, SHI-YUN WANG, TING CHENG, CHIH-WEI CHIU, PING CHAO, : "Development of glycosynthases with broad glycan specificity for the efficient glyco-remodeling of antibodies", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 54, no. 48, 1 January 2018 (2018-01-01), UK , pages 6161 - 6164, XP055612507, ISSN: 1359-7345, DOI: 10.1039/C8CC03384F
YAMANOI, T. TSUTSUMIDA, M. ODA, Y. AKAIKE, E. OSUMI, K. YAMAMOTO, K. FUJITA, K.: "Transglycosylation reaction of Mucor hiemalis endo-@b-N-acetylglucosaminidase using sugar derivatives modified at C-1 or C-2 as oligosaccharide acceptors", CARBOHYDRATE RESEARCH, PERGAMON, GB, vol. 339, no. 7, 17 May 2004 (2004-05-17), GB , pages 1403 - 1406, XP004504529, ISSN: 0008-6215, DOI: 10.1016/j.carres.2004.01.023
YOSHIYUKI MANABE; HIROKI SHOMURA; NAOYA MINAMOTO; MASAHIRO NAGASAKI; YOHEI TAKAKURA; KATSUNORI TANAKA; ALBA SILIPO; ANTONIO MOLINA: "Convergent Synthesis of a Bisecting N‐Acetylglucosamine (GlcNAc)‐Containing N‐Glycan", CHEMISTRY - AN ASIAN JOURNAL, WILEY-VCH, HOBOKEN, USA, vol. 13, no. 12, 25 May 2018 (2018-05-25), Hoboken, USA, pages 1544 - 1551, XP072430862, ISSN: 1861-4728, DOI: 10.1002/asia.201800367
TIEHAI LI; MIN HUANG; LIN LIU; SHUO WANG; KELLEY W. MOREMEN; GEERT‐JAN BOONS: "Divergent Chemoenzymatic Synthesis of Asymmetrical‐Core‐Fucosylated and Core‐Unmodified N‐Glycans", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 22, no. 52, 22 November 2016 (2016-11-22), DE, pages 18742 - 18746, XP071879700, ISSN: 0947-6539, DOI: 10.1002/chem.201604999
WANG ZHEN, ZOEISHA S. CHINOY, SHAILESH G. AMBRE, WENJIE PENG, RYAN MCBRIDE, ROBERT P. DE VRIES, JOHN GLUSHKA, JAMES C. PAULSON, GE: "A General Strategy for the Chemoenzymatic Synthesis of Asymmetrically Branched N-Glycans", SCIENCE, AMERICAN ASSOCIATION FOR THE ADVANCEMENT OF SCIENCE, US, vol. 341, no. 6144, 26 July 2013 (2013-07-26), US , pages 379 - 383, XP093146929, ISSN: 0036-8075
H. FIROUZABADI: "Science of synthesis : Houben-Weyl methods of molecular transformations: Category 4 : Compounds with two carbon-heteroatom bonds", vol. 30, 1 January 2007, STUTTGART : GEORG THIEME VERLAG. , DE , ISBN: 978-3-13-118821-2, article YAMADA, H.: "Product subclass 3: carbohydrate derivatives (including nucleosides)", pages: 47 - 81, XP009166014
TANAKA HIROSHI, IWATA YUKI, TAKAHASHI DAISUKE, ADACHI MASAATSU, TAKAHASHI TAKASHI: "Efficient Stereoselective Synthesis of γ- N -Glycosyl Asparagines by N-Glycosylation of Primary Amide Groups", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 127, no. 6, 1 February 2005 (2005-02-01), pages 1630 - 1631, XP055966235, ISSN: 0002-7863, DOI: 10.1021/ja0450298
APOORVA D. SRIVASTAVA; LUCA UNIONE; MARGREET A. WOLFERT; PABLO VALVERDE; ANA ARDÁ; JESÚS JIMÉNEZ‐BARBERO; GEERT‐JAN BOONS: "Mono‐ and Di‐Fucosylated Glycans of the Parasitic Worm S. mansoni are Recognized Differently by the Innate Immune Receptor DC‐SIGN", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 26, no. 67, 22 October 2020 (2020-10-22), DE, pages 15605 - 15612, XP072572250, ISSN: 0947-6539, DOI: 10.1002/chem.202002619
SHUAISHUAI WANG; QING ZHANG; CONGCONG CHEN; YUXI GUO; MADHUSUDHAN REDDY GADI; JIN YU; ULRIKA WESTERLIND; YUNPENG LIU; XUEFENG CAO;: "Facile Chemoenzymatic Synthesis of O‐Mannosyl Glycans", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 57, no. 30, 18 May 2018 (2018-05-18), Hoboken, USA, pages 9268 - 9273, XP072104390, ISSN: 1433-7851, DOI: 10.1002/anie.201803536
WALCZEWSKA AGATA, GRZYWACZ DARIA, BEDNARCZYK DOROTA, DAWGUL MAŁGORZATA, NOWACKI ANDRZEJ, KAMYSZ WOJCIECH, LIBEREK BEATA, MYSZKA HE: "N -Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity", BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 11, 1 January 2015 (2015-01-01), pages 869 - 874, XP055966227, DOI: 10.3762/bjoc.11.97
HUDAK JASON E., YU HELEN H., BERTOZZI CAROLYN R.: "Protein Glycoengineering Enabled by the Versatile Synthesis of Aminooxy Glycans and the Genetically Encoded Aldehyde Tag", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 133, no. 40, 12 October 2011 (2011-10-12), pages 16127 - 16135, XP055966226, ISSN: 0002-7863, DOI: 10.1021/ja206023e
TANAKA KATSUNORI, GOI TAKASHI, FUKASE KOICHI: "Highly Efficient Sialylation towards α(2-3)- and α(2-6)-Neu5Ac-Gal Synthesis: Significant ‘Fixed Dipole Effect’ of N -Phthalyl Group on α-Selectivity", SYNLETT, GEORG THIEME VERLAG, DE, vol. 2005, no. 19, 1 January 2005 (2005-01-01), DE , pages 2958 - 2962, XP055966224, ISSN: 0936-5214, DOI: 10.1055/s-2005-921889
TANAKA, SHIN-ICHI. TAKSAHI GOI. KATSUNORI TANAKA. KOICHI FUKASE: "Highly Efficient α‐Sialylation by Virtue of Fixed Dipole Effects of N‐Phthalyl Group: Application to Continuous Flow Synthesis of α(2‐3)‐and α(2‐6)‐Neu5Ac‐Gal Motifs by Microreactor", JOURNAL OF CARBOHYDRATE CHEMISTRY, TAYLOR & FRANCIS, UK, vol. 26, no. 7, 7 November 2007 (2007-11-07), UK , pages 369 - 394, XP009539487, ISSN: 0732-8303, DOI: 10.1080/07328300701634796
GUO, Z.-W. ITO, Y. NAKAHARA, Y. OGAWA, T.: "Synthetic study on a novel Asn-linked core structure: synthesis of a pentasaccharide @a-d-Man-(1@[3)-[@a-d-Man-(1@[6)]-@b-d-Man-(1@[4)-[@b-d-GlcNAc-(1@[6)]-@b-d- GlcNAc@[OMp", CARBOHYDRATE RESEARCH, PERGAMON, GB, vol. 306, no. 4, 1 January 1998 (1998-01-01), GB , pages 539 - 544, XP004127016, ISSN: 0008-6215, DOI: 10.1016/S0008-6215(98)00031-7
MITSUHIRO IWAMOTO, TAKAHIRO YAMAGUCHI, YUKIKO SEKIGUCHI, SHOHEI OISHI, TAKESHI SHIIKI, MASAKO SOMA, KENSUKE NAKAMURA, MAKOTO YOSHI: "Pharmacokinetic and Pharmacodynamic Profiles of Glyco-Modified Atrial Natriuretic Peptide Derivatives Synthesized Using Chemo-enzymatic Synthesis Approaches", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 29, no. 8, 15 August 2018 (2018-08-15), US , pages 2829 - 2837, XP055641868, ISSN: 1043-1802, DOI: 10.1021/acs.bioconjchem.8b00427
SHIVATARE SACHIN S.; CHANG SHIH-HUANG; TSAI TSUNG-I; TSENG SUSAN YU; SHIVATARE VIDYA S.; LIN YIH-SHYAN; CHENG YANG-YU; REN CHIEN-T: "Modular synthesis of-glycans and arrays for the hetero-ligand binding analysis of HIV antibodies", NATURE CHEMISTRY, NATURE PUBLISHING GROUP UK, LONDON, vol. 8, no. 4, 7 March 2016 (2016-03-07), London, pages 338 - 346, XP037134772, ISSN: 1755-4330, DOI: 10.1038/nchem.2463
LI LEI, LIU YUNPENG, MA CHENG, QU JINGYAO, CALDERON ANGIE D., WU BAOLIN, WEI NA, WANG XUAN, GUO YUXI, XIAO ZHONGYING, SONG JING, S: "Efficient chemoenzymatic synthesis of an N-glycan isomer library", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 6, no. 10, 14 September 2015 (2015-09-14), United Kingdom , pages 5652 - 5661, XP093146918, ISSN: 2041-6520, DOI: 10.1039/C5SC02025E
NAKAHARA, Y. SHIBAYAMA, S. NAKAHARA, Y. OGAWA, T.: "Rationally designed syntheses of high-mannose and complex type undecasaccharides", CARBOHYDRATE RESEARCH, PERGAMON, GB, vol. 280, no. 1, 4 January 1996 (1996-01-04), GB , pages 67 - 84, XP004018834, ISSN: 0008-6215, DOI: 10.1016/0008-6215(95)00262-6
TAKATANI M, NAKAMA T, KUBO K, MANABE S, NAKAHARA Y, ITO Y: "Synthesis of N-linked pentasaccharides with isomeric glycosidic linkage", GLYCOCONJUGATE JOURNAL, CHAPMAN & HALL, BOSTON, vol. 17, no. 6, 1 June 2000 (2000-06-01), Boston , pages 361 - 375, XP093146922, ISSN: 0282-0080, DOI: 10.1023/A:1007151913476
FAIRBANKS ANTONY J: "Synthetic and semi-synthetic approaches to unprotected N -glycan oxazolines", BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 14, 1 January 2018 (2018-01-01), pages 416 - 429, XP055966254, DOI: 10.3762/bjoc.14.30
SACHIN S. SHIVATARE, LIN-YA HUANG, YI-FANG ZENG, JUNG-YU LIAO, TSAI-HONG YOU, SHI-YUN WANG, TING CHENG, CHIH-WEI CHIU, PING CHAO, : "Development of glycosynthases with broad glycan specificity for the efficient glyco-remodeling of antibodies", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 54, no. 48, 1 January 2018 (2018-01-01), UK , pages 6161 - 6164, XP055612507, ISSN: 1359-7345, DOI: 10.1039/C8CC03384F
YAMANOI, T. TSUTSUMIDA, M. ODA, Y. AKAIKE, E. OSUMI, K. YAMAMOTO, K. FUJITA, K.: "Transglycosylation reaction of Mucor hiemalis endo-@b-N-acetylglucosaminidase using sugar derivatives modified at C-1 or C-2 as oligosaccharide acceptors", CARBOHYDRATE RESEARCH, PERGAMON, GB, vol. 339, no. 7, 17 May 2004 (2004-05-17), GB , pages 1403 - 1406, XP004504529, ISSN: 0008-6215, DOI: 10.1016/j.carres.2004.01.023
YOSHIYUKI MANABE; HIROKI SHOMURA; NAOYA MINAMOTO; MASAHIRO NAGASAKI; YOHEI TAKAKURA; KATSUNORI TANAKA; ALBA SILIPO; ANTONIO MOLINA: "Convergent Synthesis of a Bisecting N‐Acetylglucosamine (GlcNAc)‐Containing N‐Glycan", CHEMISTRY - AN ASIAN JOURNAL, WILEY-VCH, HOBOKEN, USA, vol. 13, no. 12, 25 May 2018 (2018-05-25), Hoboken, USA, pages 1544 - 1551, XP072430862, ISSN: 1861-4728, DOI: 10.1002/asia.201800367
TIEHAI LI; MIN HUANG; LIN LIU; SHUO WANG; KELLEY W. MOREMEN; GEERT‐JAN BOONS: "Divergent Chemoenzymatic Synthesis of Asymmetrical‐Core‐Fucosylated and Core‐Unmodified N‐Glycans", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 22, no. 52, 22 November 2016 (2016-11-22), DE, pages 18742 - 18746, XP071879700, ISSN: 0947-6539, DOI: 10.1002/chem.201604999
WANG ZHEN, ZOEISHA S. CHINOY, SHAILESH G. AMBRE, WENJIE PENG, RYAN MCBRIDE, ROBERT P. DE VRIES, JOHN GLUSHKA, JAMES C. PAULSON, GE: "A General Strategy for the Chemoenzymatic Synthesis of Asymmetrically Branched N-Glycans", SCIENCE, AMERICAN ASSOCIATION FOR THE ADVANCEMENT OF SCIENCE, US, vol. 341, no. 6144, 26 July 2013 (2013-07-26), US , pages 379 - 383, XP093146929, ISSN: 0036-8075
H. FIROUZABADI: "Science of synthesis : Houben-Weyl methods of molecular transformations: Category 4 : Compounds with two carbon-heteroatom bonds", vol. 30, 1 January 2007, STUTTGART : GEORG THIEME VERLAG. , DE , ISBN: 978-3-13-118821-2, article YAMADA, H.: "Product subclass 3: carbohydrate derivatives (including nucleosides)", pages: 47 - 81, XP009166014
TANAKA HIROSHI, IWATA YUKI, TAKAHASHI DAISUKE, ADACHI MASAATSU, TAKAHASHI TAKASHI: "Efficient Stereoselective Synthesis of γ- N -Glycosyl Asparagines by N-Glycosylation of Primary Amide Groups", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 127, no. 6, 1 February 2005 (2005-02-01), pages 1630 - 1631, XP055966235, ISSN: 0002-7863, DOI: 10.1021/ja0450298
APOORVA D. SRIVASTAVA; LUCA UNIONE; MARGREET A. WOLFERT; PABLO VALVERDE; ANA ARDÁ; JESÚS JIMÉNEZ‐BARBERO; GEERT‐JAN BOONS: "Mono‐ and Di‐Fucosylated Glycans of the Parasitic Worm S. mansoni are Recognized Differently by the Innate Immune Receptor DC‐SIGN", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 26, no. 67, 22 October 2020 (2020-10-22), DE, pages 15605 - 15612, XP072572250, ISSN: 0947-6539, DOI: 10.1002/chem.202002619
SHUAISHUAI WANG; QING ZHANG; CONGCONG CHEN; YUXI GUO; MADHUSUDHAN REDDY GADI; JIN YU; ULRIKA WESTERLIND; YUNPENG LIU; XUEFENG CAO;: "Facile Chemoenzymatic Synthesis of O‐Mannosyl Glycans", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 57, no. 30, 18 May 2018 (2018-05-18), Hoboken, USA, pages 9268 - 9273, XP072104390, ISSN: 1433-7851, DOI: 10.1002/anie.201803536
WALCZEWSKA AGATA, GRZYWACZ DARIA, BEDNARCZYK DOROTA, DAWGUL MAŁGORZATA, NOWACKI ANDRZEJ, KAMYSZ WOJCIECH, LIBEREK BEATA, MYSZKA HE: "N -Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity", BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 11, 1 January 2015 (2015-01-01), pages 869 - 874, XP055966227, DOI: 10.3762/bjoc.11.97
HUDAK JASON E., YU HELEN H., BERTOZZI CAROLYN R.: "Protein Glycoengineering Enabled by the Versatile Synthesis of Aminooxy Glycans and the Genetically Encoded Aldehyde Tag", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 133, no. 40, 12 October 2011 (2011-10-12), pages 16127 - 16135, XP055966226, ISSN: 0002-7863, DOI: 10.1021/ja206023e
TANAKA KATSUNORI, GOI TAKASHI, FUKASE KOICHI: "Highly Efficient Sialylation towards α(2-3)- and α(2-6)-Neu5Ac-Gal Synthesis: Significant ‘Fixed Dipole Effect’ of N -Phthalyl Group on α-Selectivity", SYNLETT, GEORG THIEME VERLAG, DE, vol. 2005, no. 19, 1 January 2005 (2005-01-01), DE , pages 2958 - 2962, XP055966224, ISSN: 0936-5214, DOI: 10.1055/s-2005-921889
TANAKA, SHIN-ICHI. TAKSAHI GOI. KATSUNORI TANAKA. KOICHI FUKASE: "Highly Efficient α‐Sialylation by Virtue of Fixed Dipole Effects of N‐Phthalyl Group: Application to Continuous Flow Synthesis of α(2‐3)‐and α(2‐6)‐Neu5Ac‐Gal Motifs by Microreactor", JOURNAL OF CARBOHYDRATE CHEMISTRY, TAYLOR & FRANCIS, UK, vol. 26, no. 7, 7 November 2007 (2007-11-07), UK , pages 369 - 394, XP009539487, ISSN: 0732-8303, DOI: 10.1080/07328300701634796
GUO, Z.-W. ITO, Y. NAKAHARA, Y. OGAWA, T.: "Synthetic study on a novel Asn-linked core structure: synthesis of a pentasaccharide @a-d-Man-(1@[3)-[@a-d-Man-(1@[6)]-@b-d-Man-(1@[4)-[@b-d-GlcNAc-(1@[6)]-@b-d- GlcNAc@[OMp", CARBOHYDRATE RESEARCH, PERGAMON, GB, vol. 306, no. 4, 1 January 1998 (1998-01-01), GB , pages 539 - 544, XP004127016, ISSN: 0008-6215, DOI: 10.1016/S0008-6215(98)00031-7
Attorney, Agent or Firm:
KAWAGUTI & PARTNERS (JP)
Download PDF: