95083-33-3

Upstream product

• 3744-87-4 Boc-(R)-Ala 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 19460-86-7 (N-methyl)-L-phenylalanine methyl ester hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 109208-68-6 C₁₃H₂₃NO₆ 

Downstream Products

• 131131-27-6 H-D-Ala-Phe-OMe trifluoroacetate 
• 94883-19-9 D-(N-tert-butoxycarbonylalanyl)-L-phenylalanine 
• 15136-19-3 c 
• 183444-82-8 {(S)-5-(2-Benzyloxycarbonylamino-ethylcarbamoyl)-5-[(S)-2-((R)-2-tert-butoxycarbonylamino-propionylamino)-3-phenyl-propionylamino]-pentyl}-carbamic acid tert-butyl ester 
• 183444-80-6 (6R,9S,12S)-9-benzyl-2,2,6,20,20-pentamethyl-4,7,10,18-tetraoxo-3,19-dioxa-5,8,11,17-tetraazahenicosane-12-carboxylic acid 

Relevant academic research and scientific papers

Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self-Assemblies

Although chiral nanostructures have been fabricated at various structural levels, the transfer and amplification of chirality from molecules to supramolecular self-assemblies are still puzzling, especially for heterochiral molecules. Herein, four series o

Pd-Catalyzed Site-Selective C(sp2)-H Olefination and Alkynylation of Phenylalanine Residues in Peptides

Pd-catalyzed site-selective C(sp2)-H olefination and alkynylation of phenylalanine residues in peptides are described. The amino acids within the peptides are used as native bidentate directing groups to facilitate C-H functionalization. This p

Pd-catalyzed intramolecular C(sp2)-H amination of phenylalanine moieties in dipeptides: Synthesis of indoline-2-carboxylate-containing dipeptides

A palladium-catalyzed intramolecular C(sp2)-H amination of phenylalanine moieties in dipeptides is described. By this protocol, a series of indoline-2-carboxylate-containing dipeptides were synthesized from dipeptides. The N-protected amino aci

Synthesis of highly substituted imidazolidine-2,4-dione (Hydantoin) through Tf2O-mediated dual activation of Boc-protected dipeptidyl compounds

Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products.

Synthesis of jasplakinolide analogues containing a novel ω-amino acid

The synthesis of the ω-amino acid 4 is described utilizing a two-dimensional synthesis strategy combined with an enzymatic differentiation of homotopic ester groups. The amino acid 4 features two non-bonded interactions that result in conformational const

Stereoselective reduction of N-hydroxy-α-iminocarbonyl-oligopeptide methyl esters with Zn-MsOH

The reduction of N-hydroxy-α-imino esters with Zn-MsOH in THF afforded α-amino esters in high yields. The reduction of N-hydroxy-α-iminocarbonyl-oligopeptide methyl esters prepared from L-phenylalanine and L-leucine di-, tri-, tetrapeptides gave the corre

An approach towards more selective anticancer agents

A promising approach towards better targeted anticancer drug therapy takes advantage of enhanced expression of proteases associated with human malignancies. Especially plasminogen activator activity has been found to be substantially increased, leading to an enhanced activity of the serine protease plasmin. Bifunctional alkylating agents, such as N-(2-chloroethyl)-N-nitrosoureas, display broad spectrum anticancer activity, but also exhibit considerable systemic toxicity. We describe here the synthesis of new N-nitrosourea-based prodrugs designed to become activated by tumor-associated proteases, to provide for enhanced antitumor activity and reduced systemic toxicity. Tripeptides representing substrates for plasmin were linked by an amide bond to N'-(2-aminoethyl)-N-(2-chloroethyl)-N-nitrosourea and the corresponding N'-methyl derivative. Synthesis and plasmin-triggered decomposition of these new tripeptide conjugates is described. Cancer cells expressing high plasminogen activator activity are highly sensitive to the new prodrugs in the presence of plasminogen, but not in its absence.

Synthesis and structure-activity relationships of deltorphin analogues

In order to study the structure-activity relationships of natural opioid deltorphins (H-Tyr-D-Met-Phe-His-Leu-Met-Asp-NH2 and H-Tyr-D-Ala-Phe-Asp[or Glu]-Val-Val-Gly-NH2), 15 analogues were synthesized by the solution method. Their a

AMINO ACIDS AND PEPTIDES. VII. PREPARATION AND APPLICATION OF A WATER-SOLUBLE ACTIVE ESTER, p-TRIMETHYLAMMONIOPHENYL ESTER

A water-soluble active ester, p-trimethylammoniophenyl ester iodide, and its nitro derivative were prepared from N-procteted amino acid and the corresponding phenol derivative by the dicyclohexylcarbodiimide method.The synthetic esters were applied to the synthesis of Leuenkephalin.Keywords--water-soluble active ester; p-trimethylammoniophenyl ester iodide; Leuenkephalin; peptide synthesis

Stereochemistry of Cyclic Dipeptides. Assignment of the Prochiral Methylenes of 1-Aminocyclopropane-1-carboxylic Acid

The two enantiomeric methylene carbons of 1-aminocyclopropane-1-carboxylic acid (ACC) were differentiated by an NMR study.Several amino acids such as L-alanine, D-alanine, and 2-aminoisobutyric acid as well as ACC were condensed with L- and/or D-phenylala