58885-35-1

Upstream product

• 158022-23-2 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(tritylthio)propanoate 
• 76-84-6 triphenylmethyl alcohol 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 21947-98-8 N-tert-butyloxycarbonyl-S-trityl-L-cysteine 
• 76-83-5 trityl chloride 
• 67-56-1 methanol 
• 2799-07-7 S-trityl-L-cysteine 
• 103213-32-7 N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine 
• 245088-56-6 Fmoc-Cys(Trt)-OMe 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 80497-22-9 Ddz-L-Alanyl-(S-Trt)-L-cystein-methylester 
• 108283-07-4 Boc-His(Ts)-Cys(Trt)-OMe 
• 161925-36-6 Fmoc-L-Cys(S-Trt)-L-Cys(S-Trt)-Ome 
• 200435-34-3 (R)-3-Tritylsulfanyl-2-(3-tritylsulfanyl-propionylamino)-propionic acid methyl ester 
• 309264-62-8 N-(4-methoxybenzoyl)-S-trityl-L-cysteine methyl ester 
• 309264-61-7 N-(4-nitrobenzoyl)-S-trityl-L-cysteine methyl ester 
• 309264-63-9 N-dihydrocinnamoyl-S-trityl-L-cysteine methyl ester 
• 357636-26-1 (2R)-2-(3-methyl-but-2-enoylamino)-3-tritylsulfanyl-propionic acid methyl ester 
• 647026-15-1 (R)-2-(2-Bromo-acetylamino)-3-tritylsulfanyl-propionic acid methyl ester 
• 647026-17-3 (R)-2-(4-Bromo-butyrylamino)-3-tritylsulfanyl-propionic acid methyl ester 
• 647026-18-4 (R)-methyl 2-(5-bromopentanamido)-3-(tritylthio)propanoate 
• 68869-57-8 C₃₃H₄₀N₂O₅S 
• 139924-70-2 Boc-Ala-Cys(Trt)-OMe 
• 68869-58-9 N-(tert-butyloxycarbonyl)phenylalanyl-S-tritylcysteine methyl ester 

Relevant academic research and scientific papers

Oxidative peptide bond formation of glycine-amino acid using 2-(aminomethyl)malononitrile as a glycine unit

Amide linkage of glycine-amino acid was synthesized by coupling of substituted 2-(aminomethyl)malononitrile as a C-terminal glycine unit and N-terminal amine using CsOAc and O2in an aqueous solution. This is a coupling reagent-free and catalyst-free peptide synthesisviaoxidative amide bond formation. Various tripeptides and tetrapeptides were synthesized efficiently and the sulfide moiety is inert even under an oxygen atmosphere.

Tubulysin Synthesis Featuring Stereoselective Catalysis and Highly Convergent Multicomponent Assembly

A concise and modular total synthesis of the highly potent N14-desacetoxytubulysin H (1) has been accomplished in 18 steps in an overall yield of up to 30percent. Our work highlights the complexity-augmenting and route-shortening power of diastereoselective multicomponent reaction (MCR) as well as the role of bulky ligands to perfectly control both the regioselective and diastereoselective synthesis of tubuphenylalanine in just two steps. The total synthesis not only provides an operationally simple and step economy but will also stimulate major advances in the development of new tubulysin analogues.

Structurally Diverse Acyl Bicyclobutanes: Valuable Strained Electrophiles

Bicyclo[1.1.0]butanes (BCBs) are highly strained carbocycles that have emerged as versatile synthetic tools, particularly for the construction of functionalized small molecules. This work reports two efficient pathways for the rapid preparation of over 20 structurally diverse BCB ketones, encompassing simple alkyl and aryl derivatives, as well as unprecedented amino acid, dipeptide, bioisostere, and bifunctional linchpin reagents currently inaccessible using literature methods. Analogues are readily forged in two steps and in high yields from simple carboxylic acids or through unsymmetrical ketone synthesis beginning with a convenient carbonyl dication equivalent. The utility of this novel toolbox of strained electrophiles for the selective modification of proteinogenic nucleophiles is highlighted.

Synthesis and stereochemistry of (?)-FE399

The stereochemistry of selective anticancer compound FE399 was determined to be rel-9R,14R,17R by theoretical and synthetic studies. Relative stereochemistry of FE399 was predicted by comparison of the 13C NMR chemical shifts of the natural sample with that predicted by theoretical calculation for each possible stereoisomer. The first synthesis of (9R,14R,17R)-(?)-FE399 was achieved using an amide formation of a dithiazocane with a hydroxy dodecanoic acid derivatives and sixteen-membered macrolactonization as key steps. The overall yield was 18% in ten steps from L-cysteine and (S)-glycidyl tosylate.

TUBULYSIN DERIVATIVES AND METHODS FOR PREPARING THE SAME

The invention relates to novel means and methods for the synthesis of tubulysin and derivatives thereof, which find their use e.g. as cytotoxic agents in targeted drug delivery. Provided is a method for preparing a tubulysin derivative, comprising reacting compounds A, B and C in a 3- component Passerini reaction, wherein compound A is a carboxylic acid according to the general formula (A); wherein compound B is an aldehyde according to the general formula (B); and wherein compound C is an isocyanide according to the general formula (C).

Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics

A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.

Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles

An alternative approach toward the simple and robust synthesis of highly substituted peptidic thiazole derivatives using Ugi-multicomponent reaction (U-MCR) is described. Thus, we introduced the enantiopure (R)-2-methyl-2-isocyano-3-(tritylthio)propanoate as a novel class of isocyanide in MCR. This bifunctional isocyanide was found to undergo mild cyclodehydration to afford thiazole containing peptidomimetics in a short synthetic sequence. Several examples of bis-heterocyclic rings were also synthesized through the proper choice of the aldehyde component in the U-4CR. The method opens a wide range of applications toward the synthesis of nonribosomal natural products and other bioactive compounds.

Polypeptide Immobilization

The present invention provides a method, comprising (a) providing a reactant ligand attached to a substrate; (b) contacting the substrate with a fusion polypeptide, said fusion polypeptide comprising a capture polypeptide fused to a display polypeptide un

Intramolecular hydrogen-bonding activation in cysteines: A new effective radical scavenger

The challenge of developing organic molecules with improved antioxidant activities for a competitive marketplace requires, given the great amount of possibilities, much laboratory work. Nowadays, the ability of methodologies based on quantum chemistry to determine the influence of different modifications on a molecule core provides a powerful tool for selecting the most useful derivatives to be synthesized. Here, we report the results of the assessment of antioxidant activity for quaternary amino acids, specifically for cysteine derivatives. The effect of introducing different substituents on the cysteine core is evaluated by using DFT to obtain an adequate structure-antioxidant activity relationship. This theoretical study shows a small panel of targets among which (R)-N-acetyl-2-methylcysteine methyl ester 15 exhibits special features and relevant antioxidant activity. The conformational 1H NMR study of this synthesized compound indicates the existence of an intramolecular C7 member ring involving S-H?OC substructure, which is reported for the first time in the literature for this amino acid unit. This unusual conformation seems to be the reason for the high antioxidant capacity experimentally found for this compound.

Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities

Following the recent output of scientific publications in the matter of synergic activity between different antioxidants, we have undertaken the present study with the aim to synthesize new molecules with radical-scavengers activity based on the conjugation of bioactive portions (i.e. phenols, cysteine, methionine or tyrosine), characterized by different structures and mechanisms of action, to promote the simultaneous quenching of different radical species in the site of the oxidative damage. In this context, derivatives of phenolic acid, aminoacids and dopamine have been also prepared. The newly synthesized compounds were evaluated in vitro applying specific and complementary antioxidant test such as DPPH assay and ORAC test. As emerged from the evaluation, prerequisites for the activity of the synthesized molecules were: i) the maintenance of at least two hydroxylic groups on the aromatic moiety of phenolic portion, ii) the presence of a spacer between the aromatic moiety and the carbonilic group.