47555-30-6

Upstream product

• 13075-31-5 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-phenylpropanoate 
• 1161-13-3 N-Cbz-L-Phe 
• 15100-75-1 L-phenylalanine tert-butyl ester hydrochloride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 35661-40-6 N-Fmoc L-Phe 
• 134996-30-8 tert-butyl 2-(tert-butylsulfonyl)-2-(propenyloxycarbonyl)phenylalanylphenylalaninate 

Downstream Products

• 1134603-40-9 C₄₅H₅₂N₄O₇ 
• 1245735-90-3 C₃₉H₄₆N₃O₇PS 
• 1323357-96-5 C₂₅H₂₆N₆O₅ 
• 1586761-24-1 C₄₀H₄₃N₃O₆S₂ 
• 1586761-32-1 C₃₆H₃₅N₃O₆S₂ 
• 211496-27-4 (S)-2-[(S)-2-((R)-2-Benzyloxycarbonylamino-2-phenyl-acetylamino)-3-phenyl-propionylamino]-3-phenyl-propionic acid 
• 96943-03-2 (S)-2-((S)-4-benzyl-2,5-dioxoimidazolidin-1-yl)-3-phenylpropanoic acid 

Relevant academic research and scientific papers

Design criteria for minimalist mimics of protein-protein interface segments

Small molecules that can interrupt or inhibit protein-protein interactions (PPIs) are valuable as probes in chemical biology and medicinal chemistry, but they are also notoriously difficult to develop. Design of non-peptidic small molecules that mimic ami

Stereocontrolled [11C]Alkylation of N-Terminal Glycine Schiff Bases To Obtain Dipeptides

The use of various quaternary ammonium salts as chiral phase-transfer catalysts allowed effective and stereoselective radiochemical [11C]alkylation to obtain functionalized dipeptides. We herein report a broadly applicable procedure for the asymmetric [11C]alkylation of dipeptides to give labeled N-terminal peptides by using different [11C]alkyl halides. Contended stereoselectivities of the reactions were observed by using 11C-labeled alkyl halides, [11C]methyl iodide and [11C]benzyl iodide, and diastereomeric ratios with different specialized catalysts of 95:5 and 90:10 were achieved, respectively. Accordingly, the straightforward synthesis of enantioenriched compounds should play a vital role in peptide-based radiopharmaceutical development and positron emission tomography imaging.

Tert-Butyl esters of peptides as organocatalysts for the asymmetric aldol reaction

Enantioselective aldol reactions between ketones and aldehydes were shown to be catalysed by a variety of tert-butyl esters of peptides. Amongst the peptides tested, Pro-Glu(OtBu)-OtBu proved to be the best, affording the product in

A dithienylethene-based rewritable hydrogelator

Dithienylethene photochromic switching units have been incorporated into a hydrogelating system based on a tripeptide motif. The resulting hybrid system provided both a photochromic response and the ability to gelate water under acidic and neutral conditi

Stereoselective self-sorting in the self-assembly of a Phe-Phe extended guanidiniocarbonyl pyrrole carboxylate zwitterion: Formation of two diastereomeric dimers with significantly different stabilities

The 'dipeptide extended' guanidiniocarbonyl pyrrole carboxylate zwitterion GCP-Phe-Phe 1 forms stable dimers in DMSO. However, dimerization is highly stereoselective. Only homochiral dimers are formed and the (L,L)·(L,L) dimer (Kdim > 105 M-1) is significantly more stable by a factor of 103 than the diastereomeric (D,L)·(D,L) dimer (Kdim = 120 M-1).

Structure-activity study of endomorphin-2 analogs with C-terminal modifications by NMR spectroscopy and molecular modeling

Endomorphin-2 (EM-2) is a putative endogenous μ-opioid receptor ligand. To get insight into the important role of C-terminal amide group of EM-2, we investigated herein a series of EM-2 analogs by substitution of the C-terminal amide group with -NHNH2, -NHCH3, -N(CH3)2, -OCH3, -OCH2CH3, -OC(CH3)3, and -CH2-OH. Their binding affinity and bioactivity were determined and compared. Despite similar (analogs 1, 4, and 7) or decreased (analogs 2, 3,5, and 6) μ affinity in binding assays, all analogs showed low guinea pig ileum (GPI) and mouse vas deferens (MVD) potencies compared to their parent peptide. Interestingly, as for analogs 2 and 3 (a single and double N-methylation of C-terminal amide), the potency order with the Ki (μ) values was 2 > 3; for the C-terminal esterified analogs 4-6, the potency order with the Ki (μ) values was 4 > 5 > 6. Thus, we concluded that the steric hindrance of C-terminus might play an important role in opioid receptor affinity. We further investigated the conformational properties of these analogs by 1D and 2D 1H NMR spectroscopy and molecular modeling. Evaluating the ratios of cis- and trans-isomers, aromatic interactions, dihedral angles, and stereoscopic views of the most convergent conformers, we found that modifications at the C-terminal amide group of EM-2 affected these analog conformations markedly, therefore changed the opioid receptor affinity and in vitro bioactivity.

Deprotection of N-tert-butoxycarbonyl (Boc) groups in the presence of tert-butyl esters

Deprotection of Boc groups in the presence of tert-butyl esters was achieved by using concentrated H2SO4 (1.5-3.0 equiv.) in tBuOAc or MeSO3H (1.5-3.0 equiv.) in tBuOAc:CH2Cl2 (4:1 v/v). The yields ranged from 70 to 100% for a variety of amino acid and dipeptide substrates. (C) 2000 Elsevier Science Ltd.

Amino-protecting groups subject to deblocking under conditions of nucleophilic addition to a Michael acceptor. Structure-Reactivity studies and use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) group

A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael acceptors showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > C6H5SO > C6H4NO2-p. The reactivity of the nucleophile (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. β- Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

Synthesis of heterodisaccharide-containing peptides, fragments of actinoidin antibiotics

Prototypes corresponding to glycopeptide fragments of actinoidin antibiotics have been synthesized using an L-acosaminyl-D-glucose-containing heterodisaccharide linked to 4-hydroxyphenylglycine as pivotal synthon. This latter compound has been obtained by coupling of a suitably protected D-glucopyranosyl bromide with the blocked amino acid, followed by selective deprotection of the glucopyranosyl moiety at C-2 and subsequent stereospecific attachment of the acosaminyl unit.

DER 2-(4-PYRIDYL)ETHOXYCARBONYL-(4-Pyoc)-REST - EINE HYDROPHILE, SAEURE- UND BASENSTABILE AMINOSCHUTZGRUPPE FUER DIE PEPTIDSYNTHESE

The title amino blocking function is stable under basic and acidic conditions frequently used in the peptide synthesis.Its hydrophilicity permits an effective peptide synthesis in water.After the easy conversion to the pyridinium form the 4-Pyoc group can