Metathesis of structurally preorganized bivalent carbohydrates. Synthesis of macrocyclic and oligomeric scaffolds

Trinidad Velasco-Torrijos; Paul V. Murphy

doi:10.1021/ol0484254

Metathesis of structurally preorganized bivalent carbohydrates. Synthesis of macrocyclic and oligomeric scaffolds

Trinidad Velasco-Torrijos
, Paul V. Murphy

University College Dublin

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

43 Citations (Scopus)

Abstract

(Chemical Equation Presented) Bivalent carbohydrate substrates for metathesis were synthesized from glucuronic acid and phenylene-1,4-diamine. The substrate secondary structure depends on whether secondary or tertiary amides are present, and this influences the course of the metathesis reaction leading to novel multivalent scaffolding. Molecular modeling suggests that a very rigid macrocyclic scaffold has potential for the development of α-helix peptidomimetics.

Original language	English
Pages (from-to)	3961-3964
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	22
DOIs	https://doi.org/10.1021/ol0484254
Publication status	Published - 28 Oct 2004
Externally published	Yes

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title = "Metathesis of structurally preorganized bivalent carbohydrates. Synthesis of macrocyclic and oligomeric scaffolds",

abstract = "(Chemical Equation Presented) Bivalent carbohydrate substrates for metathesis were synthesized from glucuronic acid and phenylene-1,4-diamine. The substrate secondary structure depends on whether secondary or tertiary amides are present, and this influences the course of the metathesis reaction leading to novel multivalent scaffolding. Molecular modeling suggests that a very rigid macrocyclic scaffold has potential for the development of α-helix peptidomimetics.",

author = "Trinidad Velasco-Torrijos and Murphy, \{Paul V.\}",

year = "2004",

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doi = "10.1021/ol0484254",

language = "English",

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journal = "Organic Letters",

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AU - Velasco-Torrijos, Trinidad

AU - Murphy, Paul V.

PY - 2004/10/28

Y1 - 2004/10/28

N2 - (Chemical Equation Presented) Bivalent carbohydrate substrates for metathesis were synthesized from glucuronic acid and phenylene-1,4-diamine. The substrate secondary structure depends on whether secondary or tertiary amides are present, and this influences the course of the metathesis reaction leading to novel multivalent scaffolding. Molecular modeling suggests that a very rigid macrocyclic scaffold has potential for the development of α-helix peptidomimetics.

AB - (Chemical Equation Presented) Bivalent carbohydrate substrates for metathesis were synthesized from glucuronic acid and phenylene-1,4-diamine. The substrate secondary structure depends on whether secondary or tertiary amides are present, and this influences the course of the metathesis reaction leading to novel multivalent scaffolding. Molecular modeling suggests that a very rigid macrocyclic scaffold has potential for the development of α-helix peptidomimetics.

UR - https://www.scopus.com/pages/publications/8744229693

U2 - 10.1021/ol0484254

DO - 10.1021/ol0484254

M3 - Article

SN - 1523-7060

VL - 6

SP - 3961

EP - 3964

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Metathesis of structurally preorganized bivalent carbohydrates. Synthesis of macrocyclic and oligomeric scaffolds

Abstract

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