7633-32-1Relevant articles and documents
COMPOSITIONS AND METHODS RELATED TO MOLECULAR CONJUGATION
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Page/Page column 56-58, (2021/06/11)
The invention relates to activated Michael acceptor (AMA) compounds that can undergo conjugation with biomolecules containing Michael donor moieties, thereby providing plasma-stable antibody-drug conjugates (ADCs). Pharmaceutical compositions of the ADCs are disclosed as well. Also provided herein are a number of applications (e.g., therapeutic applications) in which the compositions are useful.
A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling
Ni, Shengyang,Garrido-Castro, Alberto F.,Merchant, Rohan R.,de Gruyter, Justine N.,Schmitt, Daniel C.,Mousseau, James J.,Gallego, Gary M.,Yang, Shouliang,Collins, Michael R.,Qiao, Jennifer X.,Yeung, Kap-Sun,Langley, David R.,Poss, Michael A.,Scola, Paul M.,Qin, Tian,Baran, Phil S.
supporting information, p. 14560 - 14565 (2018/10/24)
The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.
A Short Synthesis of the Mould Metabolite (R)-(+)-Carolinic Acid from (S)-Lactic Acid
Linder, David,Schobert, Rainer
, p. 4564 - 4568 (2016/12/14)
(R)-(+)-Carolinic acid was prepared in seven steps and 59% yield from inexpensive benzyl l-lactate, the configuration of which was inverted by a Mitsunobu reaction with trifluoroacetate. The resulting benzyl d-lactate was cyclised by a domino addition-Wittig alkenation reaction with Ph3PCCO. The product tetronic acid was acylated with a second equivalent of this ylide to give a 3-acylylidenetetronic acid, which was olefinated directly with tert-butyl glyoxylate. The product alkene was hydrogenated and deprotected to afford pure crystalline (R)-(+)-carolinic acid, which proved inactive against Staphylococcus aureus and Escherichia coli mutant D21f2.