89969-26-6

Upstream product

• 115141-89-4 (4S)-3-(benzyloxycarbonyl)-4-(3-hydroxypropyl)-1,3-oxazolidin-5-one 
• 56-86-0 L-glutamic acid 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 148680-16-4 (S)-3-carbonylbenzyloxy-4-(2-ethylsulfanylcarbonyl-ethyl)-oxazolidin-5-one 
• 58456-26-1 (S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester 

Downstream Products

• 148680-17-5 L-3-(benzyloxycarbonyl)-4-(3,3-dimethoxypropyl)-1,3-oxazolidin-5-one 
• 89969-27-7 (S)-4-(3-Benzyloxyimino-propyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 131990-88-0 (2R,5S,8S)-1-aza-8-benzyloxycarbonylamino-9-oxo-4-thiabicyclo[3.4.0]nonane-2-carboxylic acid methyl ester 
• 127104-05-6 (4S,3'R,3''S,6''S)-<6''-2H>-4-<3-<3,6-dihydro-2,5-dimethoxy-3-(1-methylethyl)pyrazin-6-yl>-3-fluoropropyl>-3-(benzyloxycarbonyl)-5-oxazolidinone 
• 52816-28-1 N⁵-Acetyl-N⁵-benzyloxy-L-ornithin 
• 89969-28-8 δ-N-acetyl-δ-N-benzyloxy-L-ornithine 
• 89969-29-9 N⁵-acetyl-N⁵-(benzyloxy)-N²-(benzyloxycarbonyl)-L-ornithine 
• 160806-01-9 (Z)-(S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-6-((R)-1-methoxycarbonyl-ethylcarbamoyl)-hex-2-enoic acid methyl ester 
• 160248-47-5 (3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid 
• 149563-21-3 Fmoc-β-turn-dipeptide 

Relevant academic research and scientific papers

Kras inhibitory cyclic peptide compound

The following were discovered: a cyclic peptide compound that interacts with Ras; and an unnatural amino acid that is useful in the production of said cyclic peptide compound. The cyclic peptide compound was also discovered to inhibit bonding between Ras and SOS. The following were additionally discovered: a specific unnatural amino acid included in said cyclic peptide compound; and a manufacturing method therefor.

Constrained peptidomimetics reveal detailed geometric requirements of covalent prolyl oligopeptidase inhibitors

Prolyl oligopeptidases cleave peptides on the carboxy side of internal proline residues and their inhibition has potential in the treatment of human brain disorders. Using our docking program FITTED, we have designed a series of constrained covalent inhibitors, built from a series of bicyclic scaffolds, to study the optimal shape required for these small molecules. These structures bear nitrile functional groups that we predicted to covalently bind to the catalytic serine of the enzyme. Synthesis and biological assays using human brain-derived astrocytic cells and endothelial cells and human fibroblasts revealed that these compounds act as selective inhibitors of prolyl oligopeptidase activity compared to prolyl-dipeptidyl-aminopeptidase activity, are able to penetrate the cells and inhibit intracellular activities in intact living cells. This integrated computational and experimental study shed light on the binding mode of inhibitors in the enzyme active site and will guide the design of future drug-like molecules.

Improved synthesis of 7,5-fused bicyclic lactams for use as peptidomimetics

An improved synthesis of (3S, 7R, 10S)-methyl-2-oxo-3-N-phthaloylamino-1- azabicyclo[5.3.0]decane-10-carboxylate from L-glutamic acid and L-allylglycine is presented.

Synthesis of muramyl peptides containing meso-diaminopimelic acid

Chain-extension of L-glutamate aldehyde 3 by means of the Wittig-Horner reaction furnished the desired C7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D- isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanyl- L-isoglutaminyl-(2S,6R)-2,6-diaminopimelic-D-alanme (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-D- isoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Angiotensin II analogues encompassing 5,9- and 5,10-fused thiazabicycloalkane tripeptide mimetics

A simple experimental procedure on solid phase for the construction of new tripeptidic 5,9- and 5,10-fused thiazabicycloalkane scaffolds that adopt β-turns has been developed. This N-terminal-directed bicyclization, relying on masked aldehyde precursors d

Inhibitors of SH2-mediated processes

This invention relates to compounds of formula: STR1 and pharmaceutically acceptable salts thereof, where A is H, R1, --CO--R1 or --CO--OR1 where R1 is a substituted or unsubstituted alkyl, heteroalkyl, aryl or heteroaryl group and J is H or NO2. L-forms of the compounds are currently preferred, although D-forms and racemic mixtures are also encompassed by this invention.

AN ASYMMETRIC SYNTHESIS OF DIFFERENTIALLY PROTECTED MESO-2,6-DIAMINOPIMELIC ACID

Differentially protected meso-2,6-diaminopimelic acid, a component of bacterial cell walls, a biosynthetic precursor of L-lysine and a constituent of several synthetic immunostimulants, has been prepared stereospecifically from L-glutamic acid.

Cyclic hexapeptides and chimeric peptides as mimics of tendamistat

We describe the design and evaluation of structural mimics of tendamistat, a 74-residue proteinaceous inhibitor of α-amylase. Cyclic hexapeptides were designed in which the sequence Trp-Arg-Tyr is constrained to the i + 1 to i + 3 positions of a type I β-

Total synthesis of (+)-porothramycin B

The first total synthesis of (+)-porothramycin B (1b is described. Our synthetic pathway can be readily applied to the synthesis of other members of the pyrrolo[1,4]benzodiazepine antibiotics.

Synthesis of 3-fluorodiaminopimelic acid isomers as inhibitors of diaminopimelate epimerase: Stereocontrolled enzymatic elimination of hydrogen fluoride

Two hydroxylated and four fluorinated analogues of diaminopimelic acid (DAP) were synthesized in stereochemically pure form and examined for inhibition of diaminopimelate eimearase from Escherichia coli. The hydroxylated derivative of L.L-DAP, (2S,3R,6S)-