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Synthesis of labeled galactosylhydroxylysine
Author(s) -
Adamczyk Maciej,
Reddy Rajarathnam E.,
Rege Sushil D.
Publication year - 2001
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.442
Subject(s) - chemistry , hydroxylysine , yield (engineering) , hydrolysis , derivative (finance) , glycosylation , wittig reaction , galactose , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , amino acid , lysine , materials science , economics , financial economics , metallurgy
Abstract A concise synthesis of isotopically labeled galactosylhydroxylysine ( 2 ) was achieved via glycosylation of labeled hydroxylysine derivative ( 3 ) with (+)‐acetobromo‐α‐D‐galactose ( 4 ) and subsequent hydrolysis in good overall yield. The hydroxylysine derivative ( 3 ) was prepared from ( S )‐(−)‐methyl‐2‐[bis‐( tert ‐butoxycarbonyl)amino]‐5‐oxopentanoate ( 4 ) with the introduction of label ( 13 CD 2 ) via a Wittig reaction using 13 CD 3 PPh 3 I. Copyright © 2001 John Wiley & Sons, Ltd.