Application of Ugi reactions in synthesis of divalent neoglycoconjugates: Evidence that the sugars are presented in restricted conformation

Helena Bradley; Geraldine Fitzpatrick; W. Kenneth Glass; Horst Kunz; Paul V. Murphy

doi:10.1021/ol016294q

Application of Ugi reactions in synthesis of divalent neoglycoconjugates: Evidence that the sugars are presented in restricted conformation

Helena Bradley, Geraldine Fitzpatrick, W. Kenneth Glass, Horst Kunz, Paul V. Murphy

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

49 Citations (Scopus)

Abstract

(Equation presented) The Ugi reaction has been used to prepare divalent galactose derivatives. NMR analysis shows that a divalent neoglycoconjugate, where the glycopeptides are bridged by a terephthaloyl group, is an 83:17 mixture of two conformers; the amide groups of the major isomer have E-anti conformations. The spatial relationship and the relative orientation of the sugars are restricted, which may have consequences for the recognition of this and related structures in biological systems.

Original language	English
Pages (from-to)	2629-2632
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	17
DOIs	https://doi.org/10.1021/ol016294q
Publication status	Published - 23 Aug 2001
Externally published	Yes

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10.1021/ol016294q

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abstract = "(Equation presented) The Ugi reaction has been used to prepare divalent galactose derivatives. NMR analysis shows that a divalent neoglycoconjugate, where the glycopeptides are bridged by a terephthaloyl group, is an 83:17 mixture of two conformers; the amide groups of the major isomer have E-anti conformations. The spatial relationship and the relative orientation of the sugars are restricted, which may have consequences for the recognition of this and related structures in biological systems.",

author = "Helena Bradley and Geraldine Fitzpatrick and Glass, \{W. Kenneth\} and Horst Kunz and Murphy, \{Paul V.\}",

year = "2001",

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AU - Glass, W. Kenneth

AU - Kunz, Horst

AU - Murphy, Paul V.

PY - 2001/8/23

Y1 - 2001/8/23

N2 - (Equation presented) The Ugi reaction has been used to prepare divalent galactose derivatives. NMR analysis shows that a divalent neoglycoconjugate, where the glycopeptides are bridged by a terephthaloyl group, is an 83:17 mixture of two conformers; the amide groups of the major isomer have E-anti conformations. The spatial relationship and the relative orientation of the sugars are restricted, which may have consequences for the recognition of this and related structures in biological systems.

AB - (Equation presented) The Ugi reaction has been used to prepare divalent galactose derivatives. NMR analysis shows that a divalent neoglycoconjugate, where the glycopeptides are bridged by a terephthaloyl group, is an 83:17 mixture of two conformers; the amide groups of the major isomer have E-anti conformations. The spatial relationship and the relative orientation of the sugars are restricted, which may have consequences for the recognition of this and related structures in biological systems.

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DO - 10.1021/ol016294q

M3 - Article

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SP - 2629

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JO - Organic Letters

JF - Organic Letters

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ER -

Application of Ugi reactions in synthesis of divalent neoglycoconjugates: Evidence that the sugars are presented in restricted conformation

Abstract

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