Ring opening of sialyllactones with glycine esters: Synthesis of selectively protected glycinyl-NeuAc saccharopeptides

Jacquelyn Gervay-Hague; P. S. Ramamoorthy; Nellie N. Mamuya

doi:10.1016/S0040-4020(97)00364-5

Ring opening of sialyllactones with glycine esters: Synthesis of selectively protected glycinyl-NeuAc saccharopeptides

Jacquelyn Gervay-Hague, P. S. Ramamoorthy, Nellie N. Mamuya

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

Two different classes of sialyllactones were prepared as potential substrates for ring opening reactions with naturally occurring amino acids. The sialyllactones underwent reaction with Glycine ethyl ester hydrochloride salt to afford selectively protected glycine-NeuAc adducts. The reactions could be performed on NeuAc derivatives capable of serving as glycosylation donors. These compounds represent a new class of saccharopeptides, composed of sugar amino acids and naturally occurring amino acids.

Original language	English (US)
Pages (from-to)	11039-11048
Number of pages	10
Journal	Tetrahedron
Volume	53
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4020(97)00364-5
State	Published - Aug 11 1997
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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abstract = "Two different classes of sialyllactones were prepared as potential substrates for ring opening reactions with naturally occurring amino acids. The sialyllactones underwent reaction with Glycine ethyl ester hydrochloride salt to afford selectively protected glycine-NeuAc adducts. The reactions could be performed on NeuAc derivatives capable of serving as glycosylation donors. These compounds represent a new class of saccharopeptides, composed of sugar amino acids and naturally occurring amino acids.",

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AU - Mamuya, Nellie N.

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N2 - Two different classes of sialyllactones were prepared as potential substrates for ring opening reactions with naturally occurring amino acids. The sialyllactones underwent reaction with Glycine ethyl ester hydrochloride salt to afford selectively protected glycine-NeuAc adducts. The reactions could be performed on NeuAc derivatives capable of serving as glycosylation donors. These compounds represent a new class of saccharopeptides, composed of sugar amino acids and naturally occurring amino acids.

AB - Two different classes of sialyllactones were prepared as potential substrates for ring opening reactions with naturally occurring amino acids. The sialyllactones underwent reaction with Glycine ethyl ester hydrochloride salt to afford selectively protected glycine-NeuAc adducts. The reactions could be performed on NeuAc derivatives capable of serving as glycosylation donors. These compounds represent a new class of saccharopeptides, composed of sugar amino acids and naturally occurring amino acids.

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Ring opening of sialyllactones with glycine esters: Synthesis of selectively protected glycinyl-NeuAc saccharopeptides

Abstract

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