Focus Review

Stereoselective Glycosylation of Glucosamine: The Role of the N-Protecting Group

  1. Dr. Ramu Enugala,
  2. Luísa C. R. Carvalho,
  3. Marina J. Dias Pires,
  4. Dr. M. Manuel B. Marques*

Article first published online: 29 JUN 2012

DOI: 10.1002/asia.201200338

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 7, Issue 11, pages 2482–2501, November 2012

Additional Information

How to Cite

Enugala, R., Carvalho, L. C. R., Dias Pires, M. J. and Marques, M. M. B. (2012), Stereoselective Glycosylation of Glucosamine: The Role of the N-Protecting Group. Chem. Asian J., 7: 2482–2501. doi: 10.1002/asia.201200338

Author Information

  1. Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Campus de Caparica 2829-516 Caparica (Portugal), Fax: (+351) 21-294-8550

*Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Campus de Caparica 2829-516 Caparica (Portugal), Fax: (+351) 21-294-8550

Publication History

  1. Issue published online: 10 OCT 2012
  2. Article first published online: 29 JUN 2012
  3. Manuscript Received: 13 APR 2012

Funded by

  • Fundação para a Ciência e Tecnologia. Grant Numbers: SFRH/BPD/42134/2007, SFRH/BD/63407/2009

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Keywords:

  • glucosamine;
  • glycoconjugates;
  • glycosylation;
  • protecting groups;
  • stereoselectivity

Abstract

Oligosaccharides and glycoconjugates play an important role in biological processes. The use of these complex polymers as biocompatible materials for medicinal applications as well as therapeutic agents for the treatment of several diseases has attracted considerable interest. However, these investigations require large and pure amounts of glycostructures. Glucosamine is one of the major building blocks of these highly important glycoconjugates. Recently, considerable synthetic efforts have been devoted to improving stereoselective glycosylation. In this Focus review, the role of the amine protecting group in the outcome of the glucosamine glycosylation reaction is highlighted.

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Featured Compounds

Compound 1
Molecular Weight:777.8102
Molecular Formula:C41H47NO14
InChIKey:IEHHSIAVVSDWTP-SRBDJQBJSA-N
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Compound 2
Molecular Weight:777.8102
Molecular Formula:C41H47NO14
InChIKey:IEHHSIAVVSDWTP-QCISSENZSA-N
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Compound 3
Molecular Weight:437.464
Molecular Formula:C20H23NO8S
InChIKey:GWNJPNGUSXDTTN-NNIGNNQHSA-N
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Compound 4
Molecular Weight:606.6827
Molecular Formula:C34H40NO9
InChIKey:Not Available
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Compound 5
Molecular Weight:554.054
Molecular Formula:C29H28ClNO6S
InChIKey:SBQKCOYANQOYLY-LZEBPPIWSA-N
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Compound 33
Molecular Weight:260.2836
Molecular Formula:C12H20O6
InChIKey:Not Available
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Compound 6
Molecular Weight:1050.56
Molecular Formula:C57H62ClN2O15
InChIKey:Not Available
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 8
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:272.2512
Molecular Formula:C12H16O7
InChIKey:Not Available
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Compound 20
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 15
Molecular Weight:373.3154
Molecular Formula:C14H19N3O9
InChIKey:QKGHBQJLEHAMKJ-KSTCHIGDSA-N
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Compound 16
Molecular Weight:373.3154
Molecular Formula:C14H19N3O9
InChIKey:QKGHBQJLEHAMKJ-DHGKCCLASA-N
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Compound 17
Molecular Weight:373.3154
Molecular Formula:C14H19N3O9
InChIKey:QKGHBQJLEHAMKJ-XVIXHAIJSA-N
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Compound 18
Molecular Weight:215.632
Molecular Formula:C6H14ClNO5
InChIKey:QKPLRMLTKYXDST-NSEZLWDYSA-N
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Compound 19
Molecular Weight:205.1686
Molecular Formula:C6H11N3O5
InChIKey:URARQBMUQIRZQO-IVMDWMLBSA-N
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Compound 21
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 29
Molecular Weight:527.78
Molecular Formula:C20H25Cl3N2O8
InChIKey:BYSCBECWMQQCPT-XNIMBYMISA-N
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Compound 64
Molecular Weight:464.5501
Molecular Formula:C28H32O6
InChIKey:Not Available
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Compound 22
Molecular Weight:573.805
Molecular Formula:C21H27Cl3N2O10
InChIKey:ZCWYDAPPYJNASR-BCSBAJJNSA-N
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Compound 23
Molecular Weight:547.725
Molecular Formula:C18H21Cl3N2O11
InChIKey:SPSQHIDQXPENOI-ZTNWJSEGSA-N
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Compound 24
Molecular Weight:681.902
Molecular Formula:C30H27Cl3N2O10
InChIKey:WHMJXQVZBZBFKR-BJPOVAONSA-N
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Compound 25
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28
Molecular Weight:1929.9772
Molecular Formula:C79H132N16O39
InChIKey:FWMKIGMQECVEIB-HWXZUTRASA-N
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Compound 26
Molecular Weight:1683.7511
Molecular Formula:C90H98N4O28
InChIKey:ZAYVZCZYOXJEAP-JVJGZYCGSA-N
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Compound 27
Molecular Weight:1419.5188
Molecular Formula:C74H90N4O24
InChIKey:UCSHYDOMIKFPEA-VKARKEDUSA-N
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Compound 30
Molecular Weight:776.7824
Molecular Formula:C40H44N2O14
InChIKey:KGRREPBLVFYMLS-GMSZDSHNSA-N
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Compound 31
Molecular Weight:688.7188
Molecular Formula:C34H44N2O13
InChIKey:XGZFXGLNZVAGNU-LVOILJLXSA-N
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Compound 32
Molecular Weight:661.12
Molecular Formula:C16H20Cl6N2O11S
InChIKey:MSICHKODBMOZFD-SYLRKERUSA-N
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Compound 34
Molecular Weight:759.001
Molecular Formula:C26H38Cl3NO16S
InChIKey:GIOAVYHMGAKONM-JXBAXRFJSA-N
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Compound 35
Molecular Weight:557.701
Molecular Formula:C16H24Cl3N2O11P
InChIKey:WZCTVCYZDHAUIT-DHGKCCLASA-N
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Compound 45
Molecular Weight:464.5501
Molecular Formula:C28H32O6
InChIKey:ZNKMCQRFDSVZAX-RKFAPSRVSA-N
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Compound 46
Molecular Weight:642.4915
Molecular Formula:C26H25F3N4O12
InChIKey:INWMBLNJAIHKLR-BOYUVYQTSA-N
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Compound 36
Molecular Weight:415.3747
Molecular Formula:C18H26NO8P
InChIKey:XHZAOOFHYLDADP-TYENPDHQSA-N
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Compound 37
Molecular Weight:481.4328
Molecular Formula:C22H28NO9P
InChIKey:VMGOZJXNADKJDN-CGXUPHRESA-N
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Compound 38
Molecular Weight:810.6736
Molecular Formula:C32H48N2O18P2
InChIKey:CNMGAPQEMQWOTC-UUMQBWSDSA-N
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Compound 39
Molecular Weight:876.7317
Molecular Formula:C36H50N2O19P2
InChIKey:WXSOYXYVFVMDEE-WRWNZPFDSA-N
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Compound 40
Molecular Weight:447.656
Molecular Formula:C13H17Cl3N4O7
InChIKey:QFDHBBQRQWSBGV-ISUQUUIWSA-N
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Compound 41
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 42
Molecular Weight:589.828
Molecular Formula:C20H23Cl3N2O10S
InChIKey:NYKLIYDHBROKQX-DUQPFJRNSA-N
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Compound 43
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 48
Molecular Weight:466.5214
Molecular Formula:C24H34O9
InChIKey:XQTZWCPXMGVKKJ-IPLXSBJHSA-N
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Compound 44
Molecular Weight:661.558
Molecular Formula:C26H26F3N3O12S
InChIKey:MHOCAYYPJATRRJ-BOYUVYQTSA-N
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Compound 47
Molecular Weight:917.907
Molecular Formula:C46H51N3O17
InChIKey:WQTOAFKHFPLKET-RDUGCOARSA-N
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Compound 49
Molecular Weight:919.8783
Molecular Formula:C42H53N3O20
InChIKey:NXTKJHHJMJVDFT-ABJMOAMKSA-N
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Compound 50
Molecular Weight:343.3722
Molecular Formula:C16H25NO7
InChIKey:DRLDOGHUDNWFSK-RKHBJWJHSA-N
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Compound 51
Molecular Weight:501.507
Molecular Formula:C20H27N3O10S
InChIKey:DBOYFCDQWZCDOV-HLTONANMSA-N
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Compound 52
Molecular Weight:534.312
Molecular Formula:C19H24BrN3O10
InChIKey:AEQTXTWRILJUMX-QCODTGAPSA-N
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Compound 53
Molecular Weight:613.83
Molecular Formula:C22H27Cl3N4O10
InChIKey:SOYJRZYHCKHZKP-FLXNRXMOSA-N
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Compound 54
Molecular Weight:760.7019
Molecular Formula:C33H40N6O15
InChIKey:VAYMEJNUDGYSAM-QONKAJETSA-N
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Compound 55
Molecular Weight:383.779
Molecular Formula:C14H22ClNO9
InChIKey:BQLUYAHMYOLHBX-XAWYEFCRSA-N
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Compound 56
Molecular Weight:537.536
Molecular Formula:C24H27NO11S
InChIKey:VZIAXDGSDOCXMX-MRKXFKPJSA-N
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Compound 57
Molecular Weight:601.688
Molecular Formula:C29H31NO9S2
InChIKey:ZFOJWPWDDUAVIH-JPHCZMGXSA-N
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Compound 58
Molecular Weight:679.24
Molecular Formula:C42H43ClO6
InChIKey:QULPROLXWNMPEK-IGEVVBBBSA-N
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Compound 59
Molecular Weight:1244.467
Molecular Formula:C71H73NO15S2
InChIKey:HJJLLJQXEUOVPK-OLQPYRAHSA-N
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Compound 60
Molecular Weight:1108.253
Molecular Formula:C63H65NO15S
InChIKey:HWJIEJIMYKLRNW-KZBWYIPXSA-N
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Compound 61
Molecular Weight:791.9244
Molecular Formula:C47H53NO10
InChIKey:OOKCHHMEXFHXMA-RLNMGEOXSA-N
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Compound 62
Molecular Weight:1032.157
Molecular Formula:C57H61NO15S
InChIKey:ZUEAHKIATGRISV-CIOZVPCXSA-N
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Compound 65
Molecular Weight:938.1102
Molecular Formula:C57H63NO11
InChIKey:AUBFKDAGEOJLRO-RPQBDHAXSA-N
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Compound 63
Molecular Weight:416.5088
Molecular Formula:C27H28O4
InChIKey:MXYLLYBWXIUMIT-PFBJBMPXSA-N
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Compound 66
Molecular Weight:485.6447
Molecular Formula:C26H35NO6Si
InChIKey:ACMJRNDERPXSKR-UBFVSLLYSA-N
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Compound 67
Molecular Weight:374.6629
Molecular Formula:C18H38O4Si2
InChIKey:ITAWUTZFLLIOSX-BZUAXINKSA-N
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Compound 68
Molecular Weight:860.3076
Molecular Formula:C44H73NO10Si3
InChIKey:ZPXMEVAHXCFCBI-PKXRGRAPSA-N
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Compound 70
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 69
Molecular Weight:461.5064
Molecular Formula:C27H27NO6
InChIKey:ZYHVOUALXZAXNU-ZONZVBGPSA-N
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