Premium
Polyhydroxyamino‐Piperidine‐Type Iminosugars and Pipecolic Acid Analogues from a D ‐Mannose‐Derived Aldehyde
Author(s) -
Matassini Camilla,
Mirabella Stefania,
Ferhati Xhenti,
Faggi Cristina,
Robina Inmaculada,
Goti Andrea,
MorenoClavijo Elena,
MorenoVargas Antonio J.,
Cardona Francesca
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402427
Subject(s) - chemistry , reductive amination , pipecolic acid , mannose , iminosugar , aldehyde , strecker amino acid synthesis , piperidine , stereochemistry , amination , organic chemistry , amino acid , combinatorial chemistry , enantioselective synthesis , enzyme , biochemistry , catalysis
A general strategy for the synthesis of diversely substituted 3,4,5‐trihydroxypiperidines (including two natural products), 5‐amino‐3,4‐dihydroxypiperidines, 3,4,5‐trihydroxypipecolic acids, and 2‐(aminomethyl)‐3,4,5‐trihydroxypiperidines is reported. The procedure used a double reductive amination or a Strecker reaction, starting from differently protected aldehydes readily synthesized on a gram scale from D ‐mannose. The biological activities of the target compounds were evaluated, and some of them showed moderate inhibition of α‐ L ‐fucosidase and β‐glucosidase.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom