Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

Cyclic N-propargyl α-peptoids of various sizes were prepared by way of macrocyclizations of linear N-substituted oligoglycines. These compounds were used as molecular platforms to synthesize a series of iminosugar clusters with different valency and alkyl spacer lengths by means of Cu(I)-catalysed a...

Full description

Saved in:

Bibliographic Details
Published in:	Beilstein journal of organic chemistry Vol. 10; no. 1; pp. 1406 - 1412
Main Authors:	Lepage, Mathieu L, Meli, Alessandra, Bodlenner, Anne, Tarnus, Céline, De Riccardis, Francesco, Izzo, Irene, Compain, Philippe
Format:	Journal Article
Language:	English
Published:	Germany Beilstein-Institut 23-06-2014
Subjects:	Chemical Sciences Chemistry cyclopeptoids glycosidases iminosugars inhibitors Letter multivalency mutivalent glycosystems Organic chemistry cyclopeptoids inhibitors glycosidases iminosugars mutivalent glycosystems multivalency
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	Cyclic N-propargyl α-peptoids of various sizes were prepared by way of macrocyclizations of linear N-substituted oligoglycines. These compounds were used as molecular platforms to synthesize a series of iminosugar clusters with different valency and alkyl spacer lengths by means of Cu(I)-catalysed azide-alkyne cycloadditions. Evaluation of these compounds as α-mannosidase inhibitors led to significant multivalent effects and further demonstrated the decisive influence of scaffold rigidity on binding affinity enhancements.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1860-5397 1860-5397
DOI:	10.3762/bjoc.10.144