111437-25-3

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 7622-21-1 (R)-benzyl mandelate 
• 100-39-0 benzyl bromide 
• 673-06-3 D-(R)-phenylalanine 
• 828-01-3 D-phenyllactic acid 

Downstream Products

• 124735-79-1 (S)-2-((S)-1-tert-Butoxycarbonyl-2-phenyl-ethylamino)-3-phenyl-propionic acid 
• 187402-09-1 (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester 
• 174799-91-8 (S)-2-[Benzyl-(2-tert-butoxycarbonyl-ethyl)-amino]-3-phenyl-propionic acid benzyl ester 
• 192313-65-8 (S)-3-Phenyl-2-{3-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-phenoxy}-propionic acid benzyl ester 
• 198828-34-1 (S)-2-((2S,4aR,6R,7R,8R,8aS)-6-{(1R,2R)-2-[(2R,3S,4R,5R,6S)-6-(2-Allyloxycarbonyl-ethyl)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy]-cyclohexyloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-3-phenyl-propionic acid benzyl ester 
• 335275-40-6 (S)-2-{(2R,3S,4S,5R,6R)-2-Azidomethyl-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid benzyl ester 
• 335275-42-8 (S)-2-{(2R,3S,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid benzyl ester 
• 1123178-76-6 (benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosynate)-(2->3)-(2,4-di-O-acetyl-6-O-benzoyl-β-D-galactopyranosyl)-(1->3)-1,5-anhydro-2-deoxy-6-O-[(S)-1-benzoxycarbonyl-2-benzyl-ethyl]-D-lyxo-hexitol 
• 1123178-63-1 2-(trimethylsilyl)ethyl (benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosynate)-(2->3)-(2,4-di-O-acetyl-6-O-benzoyl-β-D-galactopyranosyl)-(1->3)-6-O-[(S)-1-benzoxycarbonyl-2-phenyl-ethyl]-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 

Relevant academic research and scientific papers

Selective Monovalent Galectin-8 Ligands Based on 3-Lactoylgalactoside

Galectin-8 has gained attention as a potential new pharmacological target for the treatment of various diseases, including cancer, inflammation, and disorders associated with bone mass reduction. To that end, new molecular probes are needed in order to better understand its role and its functions. Herein we aimed to improve the affinity and target selectivity of a recently published galectin-8 ligand, 3-O-[1-carboxyethyl]-β-d-galactopyranoside, by introducing modifications at positions 1 and 3 of the galactose. Affinity data measured by fluorescence polarization show that the most potent compound reached a KD of 12 μM. Furthermore, reasonable selectivity versus other galectins was achieved, making the highlighted compound a promising lead for the development of new selective and potent ligands for galectin-8 as molecular probes to examine the protein's role in cell-based and in vivo studies.

Solid-phase synthesis and biological evaluation of a teleocidin library - Discovery of a selective PKCδ down regulator

Protein kinase C (PKC) is linked to the signal-induced modulation of a wide variety of cellular processes, such as growth, differentiation, secretion, apoptosis, and tumor development. The design and synthesis of small molecules that regulate these different cellular signaling systems is at the forefront of modern drug design. Herein we report a) an efficient method for the synthesis of indolactam V (6), a PKC activator, and its N13-des(methyl) analogues (19) using a regioselective organometallic transformation, a convenient aminomalonate derivative (10) to introduce the appropriate functionality and an enantiospecific enzymic hydrolysis as key steps; b) the use of this method in the first solid-phase synthesis of a teleocidin library modifying the N-13, C-12 and C-7 alkyl chains, and, therefore, producing a library of potential activators and/or inhibitors of PKC of the general structure (32); c) the activation of PKC by selected members of the library using a MARCKS translocation in vivo assay system; d) the observation that some of these analogues are nearly as effective as the natural PKC activators phorbol dibutyrate and (-)-indolactam V (6), and e) the observation that some of these analogues have different potential to induce down-regulation of members of the PKC gene family after chronic stimulation.

Synthesis of (15)N-Labelled Chiral Boc-Amino Acids from Triflates: Enantiomers of Leucine and Phenylalanine

An efficient synthesis of (15)N-labelled chiral Boc-amino acids by triflate alkylation of di-tert-butyl iminodicarbonate is reported.Both enantiomers of Boc-Leucine and -phenylalanine were synthesized from commercial α-amino acids of opposite configuration via α-hydroxy carboxylic acids provided by diazotization, thus extending the scope of an earlier exploratory study.The high chiral purity of the final products was confirmed by HPLC.These labelled amino acid derivatives are suitable for direct application to the synthesis of labelled peptides.