Semisynthesis of Complex-Type Biantennary Oligosaccharides Containing Lactosamine Repeating Units from a Biantennary Oligosaccharide Isolated from a Natural Source

Poly-N-acetyllactosamine (poly-LacNAc) structures on glycoproteins play important roles in essential biological events such as cell–cell adhesion. Here, we report a new strategy for the semisynthesis of LacNAc-extended complex-type biantennary oligosaccharides. We found an efficient isopropylidenati...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2018-01, Vol.83 (1), p.443-451
Main Authors: Maki, Yuta, Mima, Takanori, Okamoto, Ryo, Izumi, Masayuki, Kajihara, Yasuhiro
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a399t-b11ee035032cbc61974d56958ad218bbf5afc38bc519f286f82a6271af4a86d83
cites cdi_FETCH-LOGICAL-a399t-b11ee035032cbc61974d56958ad218bbf5afc38bc519f286f82a6271af4a86d83
container_end_page 451
container_issue 1
container_start_page 443
container_title Journal of organic chemistry
container_volume 83
creator Maki, Yuta
Mima, Takanori
Okamoto, Ryo
Izumi, Masayuki
Kajihara, Yasuhiro
description Poly-N-acetyllactosamine (poly-LacNAc) structures on glycoproteins play important roles in essential biological events such as cell–cell adhesion. Here, we report a new strategy for the semisynthesis of LacNAc-extended complex-type biantennary oligosaccharides. We found an efficient isopropylidenation reaction that selectively protects the terminal Gal-3,4-OH of a biantennary complex-type nonasaccharide isolated from a natural source. This finding enabled the conversion of the nonasaccharide into the two types of oligosaccharides containing di-LacNAc units at one or two antennae via ten-step chemical sequences.
doi_str_mv 10.1021/acs.joc.7b02485
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1978321006</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1978321006</sourcerecordid><originalsourceid>FETCH-LOGICAL-a399t-b11ee035032cbc61974d56958ad218bbf5afc38bc519f286f82a6271af4a86d83</originalsourceid><addsrcrecordid>eNp9kU1r3DAQhkVpSLZpzr0FHQvBG0m2vPIxWfoRWBJokrMZy6NEwZYcSYbu78kfrZbd9NbqMqB55oWZh5AvnC05E_wSdFy-eL1cdUxUSn4gCy4FK-qGVR_JgjEhilLU5Qn5FOMLy09KeUxORCOqhlerBXm7x9HGrUvPGG2k3tC1H6cBfxcP2wnptQWX0DkIW3o32CcfQetnCLbHmEmXwDrrnugGdMq90Tqkv3BCSLvfR2dTpCb4kcL_ouhN9AMk7N_ZW0hzgIHe-zlo_EyODAwRzw71lDx-__aw_lls7n7crK82BZRNk4qOc0RWSlYK3emaN6uql3UjFfSCq64zEowuVaclb4xQtVECarHiYCpQda_KU_J1nzsF_zpjTG0-jcZhAId-jm1OVKXgjNUZvdyjOvgYA5p2CnbMq7WctTszbTbTZjPtwUyeOD-Ez92I_V_-XUUGLvbAfnIOLu_6z7g_C9KdUQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1978321006</pqid></control><display><type>article</type><title>Semisynthesis of Complex-Type Biantennary Oligosaccharides Containing Lactosamine Repeating Units from a Biantennary Oligosaccharide Isolated from a Natural Source</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Maki, Yuta ; Mima, Takanori ; Okamoto, Ryo ; Izumi, Masayuki ; Kajihara, Yasuhiro</creator><creatorcontrib>Maki, Yuta ; Mima, Takanori ; Okamoto, Ryo ; Izumi, Masayuki ; Kajihara, Yasuhiro</creatorcontrib><description>Poly-N-acetyllactosamine (poly-LacNAc) structures on glycoproteins play important roles in essential biological events such as cell–cell adhesion. Here, we report a new strategy for the semisynthesis of LacNAc-extended complex-type biantennary oligosaccharides. We found an efficient isopropylidenation reaction that selectively protects the terminal Gal-3,4-OH of a biantennary complex-type nonasaccharide isolated from a natural source. This finding enabled the conversion of the nonasaccharide into the two types of oligosaccharides containing di-LacNAc units at one or two antennae via ten-step chemical sequences.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.7b02485</identifier><identifier>PMID: 29249147</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2018-01, Vol.83 (1), p.443-451</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a399t-b11ee035032cbc61974d56958ad218bbf5afc38bc519f286f82a6271af4a86d83</citedby><cites>FETCH-LOGICAL-a399t-b11ee035032cbc61974d56958ad218bbf5afc38bc519f286f82a6271af4a86d83</cites><orcidid>0000-0002-5838-302X ; 0000-0002-6656-2394 ; 0000-0001-9529-2525 ; 0000-0001-6486-9678</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29249147$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Maki, Yuta</creatorcontrib><creatorcontrib>Mima, Takanori</creatorcontrib><creatorcontrib>Okamoto, Ryo</creatorcontrib><creatorcontrib>Izumi, Masayuki</creatorcontrib><creatorcontrib>Kajihara, Yasuhiro</creatorcontrib><title>Semisynthesis of Complex-Type Biantennary Oligosaccharides Containing Lactosamine Repeating Units from a Biantennary Oligosaccharide Isolated from a Natural Source</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Poly-N-acetyllactosamine (poly-LacNAc) structures on glycoproteins play important roles in essential biological events such as cell–cell adhesion. Here, we report a new strategy for the semisynthesis of LacNAc-extended complex-type biantennary oligosaccharides. We found an efficient isopropylidenation reaction that selectively protects the terminal Gal-3,4-OH of a biantennary complex-type nonasaccharide isolated from a natural source. This finding enabled the conversion of the nonasaccharide into the two types of oligosaccharides containing di-LacNAc units at one or two antennae via ten-step chemical sequences.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kU1r3DAQhkVpSLZpzr0FHQvBG0m2vPIxWfoRWBJokrMZy6NEwZYcSYbu78kfrZbd9NbqMqB55oWZh5AvnC05E_wSdFy-eL1cdUxUSn4gCy4FK-qGVR_JgjEhilLU5Qn5FOMLy09KeUxORCOqhlerBXm7x9HGrUvPGG2k3tC1H6cBfxcP2wnptQWX0DkIW3o32CcfQetnCLbHmEmXwDrrnugGdMq90Tqkv3BCSLvfR2dTpCb4kcL_ouhN9AMk7N_ZW0hzgIHe-zlo_EyODAwRzw71lDx-__aw_lls7n7crK82BZRNk4qOc0RWSlYK3emaN6uql3UjFfSCq64zEowuVaclb4xQtVECarHiYCpQda_KU_J1nzsF_zpjTG0-jcZhAId-jm1OVKXgjNUZvdyjOvgYA5p2CnbMq7WctTszbTbTZjPtwUyeOD-Ez92I_V_-XUUGLvbAfnIOLu_6z7g_C9KdUQ</recordid><startdate>20180105</startdate><enddate>20180105</enddate><creator>Maki, Yuta</creator><creator>Mima, Takanori</creator><creator>Okamoto, Ryo</creator><creator>Izumi, Masayuki</creator><creator>Kajihara, Yasuhiro</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5838-302X</orcidid><orcidid>https://orcid.org/0000-0002-6656-2394</orcidid><orcidid>https://orcid.org/0000-0001-9529-2525</orcidid><orcidid>https://orcid.org/0000-0001-6486-9678</orcidid></search><sort><creationdate>20180105</creationdate><title>Semisynthesis of Complex-Type Biantennary Oligosaccharides Containing Lactosamine Repeating Units from a Biantennary Oligosaccharide Isolated from a Natural Source</title><author>Maki, Yuta ; Mima, Takanori ; Okamoto, Ryo ; Izumi, Masayuki ; Kajihara, Yasuhiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a399t-b11ee035032cbc61974d56958ad218bbf5afc38bc519f286f82a6271af4a86d83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Maki, Yuta</creatorcontrib><creatorcontrib>Mima, Takanori</creatorcontrib><creatorcontrib>Okamoto, Ryo</creatorcontrib><creatorcontrib>Izumi, Masayuki</creatorcontrib><creatorcontrib>Kajihara, Yasuhiro</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Maki, Yuta</au><au>Mima, Takanori</au><au>Okamoto, Ryo</au><au>Izumi, Masayuki</au><au>Kajihara, Yasuhiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Semisynthesis of Complex-Type Biantennary Oligosaccharides Containing Lactosamine Repeating Units from a Biantennary Oligosaccharide Isolated from a Natural Source</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2018-01-05</date><risdate>2018</risdate><volume>83</volume><issue>1</issue><spage>443</spage><epage>451</epage><pages>443-451</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Poly-N-acetyllactosamine (poly-LacNAc) structures on glycoproteins play important roles in essential biological events such as cell–cell adhesion. Here, we report a new strategy for the semisynthesis of LacNAc-extended complex-type biantennary oligosaccharides. We found an efficient isopropylidenation reaction that selectively protects the terminal Gal-3,4-OH of a biantennary complex-type nonasaccharide isolated from a natural source. This finding enabled the conversion of the nonasaccharide into the two types of oligosaccharides containing di-LacNAc units at one or two antennae via ten-step chemical sequences.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>29249147</pmid><doi>10.1021/acs.joc.7b02485</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-5838-302X</orcidid><orcidid>https://orcid.org/0000-0002-6656-2394</orcidid><orcidid>https://orcid.org/0000-0001-9529-2525</orcidid><orcidid>https://orcid.org/0000-0001-6486-9678</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2018-01, Vol.83 (1), p.443-451
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1978321006
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Semisynthesis of Complex-Type Biantennary Oligosaccharides Containing Lactosamine Repeating Units from a Biantennary Oligosaccharide Isolated from a Natural Source
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T22%3A43%3A51IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Semisynthesis%20of%20Complex-Type%20Biantennary%20Oligosaccharides%20Containing%20Lactosamine%20Repeating%20Units%20from%20a%20Biantennary%20Oligosaccharide%20Isolated%20from%20a%20Natural%20Source&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Maki,%20Yuta&rft.date=2018-01-05&rft.volume=83&rft.issue=1&rft.spage=443&rft.epage=451&rft.pages=443-451&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.7b02485&rft_dat=%3Cproquest_cross%3E1978321006%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a399t-b11ee035032cbc61974d56958ad218bbf5afc38bc519f286f82a6271af4a86d83%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1978321006&rft_id=info:pmid/29249147&rfr_iscdi=true