188476-33-7Relevant articles and documents
Facile stereospecific synthesis and biological evaluation of (S)- and (R)-2-amino-2-methyl-4-[123I]iodo-3-(E)-butenoic acid for brain tumor imaging with single photon emission computerized tomography
Yu, Weiping,McConathy, Jonathan,Olson, Jeffrey,Camp, Vernon M.,Goodman, Mark M.
, p. 6718 - 6721 (2007)
Both enantiomers of 2-amino-2-methyl-4-iodo-3-(E)-butenoic acid (IVAIB, 5) were radioiodoinated in 65-72% yield. (S)-IVAIB entered 9L gliosarcoma cells primarily via A-type transport in vitro with higher uptake than (R)-IVAIB. Biodistribution studies in rats with 9L gliosarcoma brain tumors demonstrated higher tumor to brain ratios with (S)-IVAIB (75:1 at 1 h) than (R)-IVAIB (7.7:1). In this model, (S)-IVAIB is superior to (R)-IVAIB and is a promising radiotracer for brain tumor imaging.
Method for producing an optically active homoserine deriv. α-
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Paragraph 0071; 0072; 0073; 0074, (2019/05/25)
PROBLEM TO BE SOLVED: To provide a method for obtaining an optically-active α-alkylserine derivative from a 1,3-propanediol derivative. SOLUTION: The method is provided, which produces an optically-active α-alkylserine derivative, such as (R) or (S)
Complementary syntheses of N,O-protected-(S)-2-methylserine on a multikilogram scale
Anson, Michael S.,Clark, Hugh F.,Evans, Paul,Fox, Martin E.,Graham, Jonathan P.,Griffiths, Natalie N.,Meek, Graham,Ramsden, James A.,Roberts, Alastair J.,Simmonds, Shaun,Walker, Matthew D.,Willets, Matthew
supporting information; experimental part, p. 389 - 397 (2012/02/02)
Two complementary and scalable approaches have been used to manufacture multikilogram quantities of N,O-protected-(S)-2-methylserine. The first approach uses a diastereomeric salt resolution of 2-methylserine methyl ester as the (1S)-(+)-camphorsulfonate salt, and was used to rapidly access 15 kg of (S)-3-tert-butoxycarbonyl-2,2,4-trimethyl-1,3-oxazolidine-4-carboxylic acid with >99% ee. The second approach involves a stereoselective enolate methylation of a chiral cyclic l-serine derivative under cryogenic conditions. The four-step telescoped process, starting from l-serine methyl ester, was used to manufacture 20 kg of (2R,4S)-2-tert-butyl-3-tert-butoxycarbonyl-4-methyl-1,3- oxazolidine-4-carboxylic acid in 52% overall yield and 98% ee. The advantages and disadvantages for scale-up of both approaches are discussed.
Enantioselective electrophilic amination of α-cyanothioacetates with azodicarboxylates catalyzed by an axially chiral guanidine base
Terada, Masahiro,Tsushima, Daisuke,Nakano, Megumi
supporting information; experimental part, p. 2817 - 2821 (2010/03/05)
An enantioselective electrophilic amination of α-substituted cyanothioacetates with azodicarboxylate is demonstrated using an axially chiral guanidine as a chiral Bronsted base catalyst. The corresponding product, having a quaternary stereogenie center at
AGONISTS OF THE SPHINGOSINE- 1- PHOSPHATE RECEPTOR (SLP)
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Page/Page column 124-125, (2008/06/13)
The invention provides compounds of formula I and formula II, their preparation, a their use as pharmaceutically active immunosuppressive agents for the treatment of autoimmune disorders, organ transplant rejection, disorders associated with an activated immune system, as well as other disorders modulated by lymphopenia or SlP receptors.
CHEMICAL COMPOUNDS
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Page/Page column 146-147, (2008/06/13)
The invention provides compounds formula I, their preparation, and their use as pharmaceutically active immunosuppressive agents for the treatment of autoimmune disorders, organ transplant rejection, disorders associated with an activated immune system, a
Synthesis of an immunomodulator (+)-conagenin and its analogs
Yakura, Takayuki,Yoshimoto, Yuya,Ishida, Chisaki,Mabuchi, Shunsuke
, p. 4429 - 4438 (2008/02/02)
Stereoselective synthesis of an immunomodulator (+)-conagenin was achieved. Both amine and carboxylic acid moieties were prepared from commercially available optically active methyl 3-hydroxy-2-methylpropanoate using dirhodium(II)-catalyzed C-H amination
Asymmetric total syntheses of marine cyclic depsipeptide halipeptins A-D
Yu, Shouyun,Pan, Xianhua,Ma, Dawei
, p. 6572 - 6584 (2008/09/16)
Halipeptins A-D (1a-d) are a family of natural cyclic depsipeptides isolated from marine sponges. Total syntheses of these four compounds are detailed in this report. The key elements in this synthesis include the elaboration of the polysubstituted decanoic acid parts by two asymmetric aldol reactions, assembly of the N-methyl-δ-hydroxyisoleucine residue by using either aza-Claisen rearrangement or methylation of aspartates as the key steps, and macrocyclization at the polysubstituted decanoic acid alanine site.
Total synthesis of (+)-conagenin
Chakraborty, Tushar Kanti,Sudhakar, Gangarajula
, p. 5847 - 5849 (2007/10/03)
The total synthesis of the immunomodulator, (+)-conagenin was achieved using, as a key step, a method developed by us for the synthesis of 2-methyl-1,3-diols via Ti(III)-mediated diastereo- and regioselective opening of trisubstituted 2,3-epoxy alcohols,
Synthesis and biological evaluation of two chemically modified peptide epitopes for the class i MHC protein HLA-B*2705
Jones, Matthew A.,Hislop, Andrew D.,Snaith, John S.
, p. 3769 - 3777 (2008/09/18)
The T-cell receptor of a CD8+ T-cell recognises peptide epitopes bound by class I major histocompatibility complex (MHC) glycoproteins presented in a groove on their upper surface. Within the groove of the MHC molecule are 6 pockets, two of whi