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Synthesis of 15 N‐Labelled D‐Isovaline and α‐Aminoisobutyric Acid
Author(s) -
Ogrel Andrei,
Shvets Vitalii I.,
Kaptein Bernard,
Broxterman Quirinus B.,
Raap Jan
Publication year - 2000
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/(sici)1099-0690(200003)2000:5<857::aid-ejoc857>3.0.co;2-v
Subject(s) - chemistry , strecker amino acid synthesis , aminoisobutyric acid , nitrile , yield (engineering) , amino acid , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , enantioselective synthesis , catalysis , materials science , metallurgy
[ 15 N]‐ D ‐isovaline was prepared from DL ‐[α‐ 15 N]‐α‐aminoisovaleramide by enzymatic resolution with Mycobacterium neoaurum . The 15 N‐isotope was introduced during the Strecker synthesis of its precursor, e.g. aminoisovaleronitrile. Attempts to prepare the amino nitrile precursor of [ 15 N]‐α‐aminoisobutyric acid (Aib) led to a poor yield and loss of the label. Significantly, improved results were obtained when a cosolvent is present during formation of aminoisobutyronitrile.