166301-19-5Relevant academic research and scientific papers
Access to any site-directed isotopomer of methionine, selenomethionine, cysteine, and selenocysteine - Use of simple, efficient modular synthetic reaction schemes for isotope incorporation
Siebum, Arjan H. G.,Woo, Wei Sein,Raap, Jan,Lugtenburg, Johan
, p. 2905 - 2913 (2007/10/03)
Simple modular reaction schemes that allow access to any isotopomer of protected serine and homoserine have been worked out. These systems could be simply converted into cysteine, selenocysteine, homocysteine, homoselenocysteine, the essential amino acid methionine, and selenomethionine by Mitsunobu chemistry. These sulfur- and selenium-containing amino acids fulfil many essential roles in the living organism. In addition, homoserine could be converted in a few steps into optically active L-vinylglycine. As well as the stable isotopes 13C, 15N, 17O, and 18O, the radioactive isotopes of sulfur, selenium and carbon can also be easily introduced in a site-directed fashion. In view of the wide scope of the Mitsunobu reaction, we feel that many more important systems with the carbon skeleton of serine and homoserine should be preparable through this basic chemistry in any site-directed isotopically labeled form. Wiley-VCH Verlag GmbH & Co, KGaA, 69451 Weinheim, Germany, 2004.
Following an ISES lead: The first examples of asymmetric Ni(0)-mediated allylic amination
Berkowitz, David B.,Maiti, Gourhari
, p. 2661 - 2664 (2007/10/03)
An ISES (in situ enzymatic screening) lead pointed to conditions (PMP N-protecting group, Ni(cod)2 catalyst precursor) under which chiral, bidentate phosphines could promote Ni(0)-mediated allylic amination. Therefore, bidentate phosphines bear
In situ enzymatic screening (ISES): A tool for catalyst discovery and reaction development
Berkowitz, David B.,Bose, Mohua,Choi, Sungjo
, p. 1603 - 1607 (2007/10/03)
Can enzymes help organic chemists identify new transition-metal catalysts? The first example of the in situ enzymatic monitoring of an organic transformation is described. Thus, a transition-metal-mediated allylic-amination reaction in the organic layer (
A convenient synthesis of L-α-vinylglycine from L-homoserine lactone
Berkowitz, David B.,Smith, Marianne K.
, p. 39 - 41 (2007/10/03)
A procedure for the synthesis of L-α-vinylglycine from L-homoserine lactone is described. The route developed is convenient (only one chromatography step is required) and efficient (72%; ≥95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Boc) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.
