3397-32-8

Basic information

• Product Name: Z-PHE-OSU
• Synonyms: CBZ-L-PHENYLALANINE HYDROXYSUCCINIMIDE ESTER;BENZYLOXYCARBONYL-L-PHENYLALANINE N-HYDROXYSUCCINIMIDE ESTER;N-CARBOBENZOXY-L-PHENYLALANINE-N-HYDROXYSUCCINIMIDE ESTER;N-ALPHA-CBZ-L-PHENYLALANINE N-HYDROXYSUCCINIMIDE ESTER;Z-PHENYLALANINE-OSU;Z-PHE-OSU;Z-L-PHENYLALANINE HYDROXYSUCCINIMIDE ESTER;Z-L-PHENYLALANINE N-HYDROXYSUCCINIMIDE ESTER
• CAS NO: 3397-32-8
• Molecular Formula: C₂₁H₂₀N₂O₆
• Molecular Weight: 396.39
• EINECS: 222-254-3
• Mol File: 3397-32-8.mol

Chemical Properties

• Melting Point: 140-140.5 °C
• Appearance: /Solid
• Density: 1.35 g/cm³
• Refractive Index: 1.617
• Storage Temp.: -15°C
• PKA: 10.56±0.46(Predicted)
• CAS DataBase Reference: Z-PHE-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PHE-OSU(3397-32-8)
• EPA Substance Registry System: Z-PHE-OSU(3397-32-8)

Safety Data

• Hazardous Substances Data: 3397-32-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Z-PHE-OSU is used as a coupling reagent for improving the efficiency and yield of peptide synthesis, which is essential for the development of new drugs and therapeutic agents.
Used in Biochemistry Research:
Z-PHE-OSU is used as a tool for the selective formation of peptide bonds, enabling researchers to study the structure and function of peptides and their interactions with other biomolecules.
Used in Peptide Synthesis:
Z-PHE-OSU is used as a reagent to facilitate the formation of peptide bonds in the synthesis of peptides, which are crucial components of proteins and have various biological functions.
Used in Laboratory Settings:
Z-PHE-OSU is used as a component in laboratory protocols for the production of peptides, providing greater control over reaction conditions and enhancing the overall success of peptide synthesis reactions.

InChI:InChI=1/C21H20N2O6/c24-18-11-12-19(25)23(18)29-20(26)17(13-15-7-3-1-4-8-15)22-21(27)28-14-16-9-5-2-6-10-16/h1-10,17H,11-14H2,(H,22,27)/t17-/m1/s1

Upstream product

• 1161-13-3 N-Cbz-L-Phe 
• 74124-79-1 di(succinimido) carbonate 
• 501-53-1 benzyl chloroformate 
• 63-91-2 L-phenylalanine 
• 96935-01-2 Isopropenyl Succinimido Carbonate 
• 57296-03-4 N,N’-disuccinimidyl oxalate 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 107960-02-1 1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate 

Downstream Products

• 16305-23-0 N-Benzyloxycarbonyl-Phe-Val-tert.-butyloxycarbonyl-hydrazid 
• 60668-59-9 [(N-benzyloxycarbonyl-L-phenylalanyl-L-phenylalanyl)amino]-methylphosphonic acid 
• 19391-50-5 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-(4-hydroxyphenyl)propanoate 
• 60668-54-4 (1R)-1-[(N-benzyloxycarbonyl-L-phenylalanyl)amino]-ethylphosphonic acid 
• 60668-14-6 [(N-benzyloxycarbonyl-L-phenylalanyl)amino]-methylphosphonic acid 
• 6464-79-5 Z-Phe-Arg(NO₂)-OCH₃ 
• 21887-86-5 N-benzyloxycarbonyl-L-phenylalanine hydrazide 
• 6464-67-1 Z-Phe-Citr 
• 6464-78-4 (S)-2-((S)-2-benzyloxycarbonylamino-3-phenylpropanoylamino)-5-nitroguanidinopentanoic acid 
• 97259-48-8 (S)-5-({Amino-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-2-((S)-2-benzyloxycarbonylamino-3-phenyl-propionylamino)-pentanoic acid 
• 159857-88-2 N-Cbz-Phe-Lys(ε-Alloc)OH 
• 953393-41-4 [(S)-1-(Anthracen-1-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 17224-88-3 benzyl ((S)-1-(((S)-1-hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 135684-45-6 3-[N-(benzyloxycarbonyl-(S)-phenylalanyl)amino]propan-1-ol 

Relevant articles and documents

Novel peptidomimetic macrocycles showing exciplex fluorescence

The synthesis of five new chiral macrocyclic peptidomimetic naphthalenophanes, together with two open-chain derivatives, is described. The cyclization step is accomplished in good yields without the use of high dilution or template techniques. The new compounds have been photophysically studied by means of steady-state fluorescence spectroscopy. It has been found that the smaller the ring size, the higher the emission quantum yield from the excited charge-transfer state (CTS, exciplex) and the lower the fluorescence from the locally excited state (LES). The occurrence of exciplex fluorescence is noteworthy as the electron-donating groups are secondary amine moieties, which do not normally form emissive exciplexes.

Fluorescent macrocyclic probes with pendant functional groups as markers of acidic organelles within live cells

A new family of acidity sensitive fluorescent macrocycles has been synthesized and fully characterized. Their photophysical properties including emission quantum yield and fluorescence lifetime have been determined. The acid-base properties of the new molecules can be tuned by the incorporation of pendant functional groups. The nature of such functional groups (carboxylic acid or ester) influences dramatically the pKa of the probes, two compounds of which exhibit low values. Preliminary intracellular studies using confocal microscopy together with emission spectra of the probes from the cellular environment have shown that the synthesized fluorescent macrocycles mark the acidic organelles of RAW 264.7 macrophage cells.

Ynamide-Mediated Thiopeptide Synthesis

Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2, and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.

2-methoxy estradiol analogs and method for preparation thereof and use

The invention relates to a 2-methoxy-estradiol analogue and a preparation method and application thereof, aiming to solve the problem of preparation of the 2-methoxy-estradiol analogue and realize the application of the 2-methoxy-estradiol analogue to preparation of anti-tumor medicaments. The method comprises the following steps: dissolving 2-methoxy-3-benzyloxy-estradiol-1,3,5-(10)-triene-17beta-alcohol or 17beta-amine serving as a raw material into an organic solvent; in the presence of Lewis alkali, carrying out an acylation reaction on the raw materials and a compound (1) to obtain a 2-methoxy-3-benzyloxy-estradiol-1,3,5-(10)-triene-17beta-ester or 17beta-amide compound (2); carrying out a catalytic hydrogenation to obtain a compound (3); carrying out an acylation reaction or a hydrocarbylation reaction to obtain a compound, namely, the 2-methoxy-estradiol analogue (4), wherein a reaction formula is shown in the specifications. The preparation method of the 2-methoxy-estradiol analogue has the advantages of easiness, mild conditions and high yield, and can be effectively applied to development of anti-tumor medicaments.

Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with α-amino amide ligands

The enantioselective alkylation of aldehydes catalysed by nickel(ii)-complexes derived from α-amino amides was studied by means of density functional theory (DFT) and ONIOM (B3LYP:UFF) calculations. A mechanism was proposed in order to investigate the origin of enantioselectivity. The chirality-determining step for the alkylation was the formation of the intermediate complexes with the involvement of a 5/4/4-fused tricyclic transition state. The predominant products predicted theoretically were of (S)-configuration, in good agreement with experimental observations. The scope of the reaction was examined and high yields and enantioselectivities were observed for the enantioselective addition of Et2Zn and Me2Zn to aromatic and aliphatic aldehydes.

Solventless mechanosynthesis of N-protected amino esters

Mechanochemical derivatizations of N- or C-protected amino acids were performed in a ball mill under solvent-free conditions. A vibrational ball mill was used for the preparation of N-protected α- and β-amino esters starting from the corresponding N-unmasked precursors via a carbamoylation reaction in the presence of di-tert-butyl dicarbonate (Boc2O), benzyl chloroformate (Z-Cl) or 9-fluorenylmethoxycarbonyl chloroformate (Fmoc-Cl). A planetary ball mill proved to be more suitable for the synthesis of amino esters from N-protected amino acids via a one-pot activation/esterification reaction in the presence of various dialkyl dicarbonates or chloroformates. The spot-to-spot reactions were straightforward, leading to the final products in reduced reaction times with improved yields and simplified work-up procedures.

Structural insight into the aggregation of l-prolyl dipeptides and its effect on organocatalytic performance

NMR and organocatalytic studies of four dipeptides derived from l-proline are described. Results indicate that important conformational changes around the catalytic l-proline moiety are observed for free dipeptides upon changing the adjacent amino acid. Also, an aggregation process is detected as the concentration increases. The self-association of the dipeptides has been fitted to a cooperative binding model. All the compounds have been assayed as catalysts for the conjugated addition of cyclohexanone to trans-β-nitrostyrene in toluene. In agreement with the structural studies, noticeable changes in the catalytic performance are detected upon changing the catalyst concentration, as the catalyst is activated by self-aggregation. This journal is

Bis(amino amides) derived from natural amino acids as chiral receptors for N-protected dicarboxylic amino acids

A family of bis(amino amides) derived from natural amino acids has been synthesized and tested for the NMR enantiodiscrimination, as chiral receptors, of some N-protected dicarboxylic amino acids. The influence of the amino acid side chain is an important parameter to obtain good enantiodiscrimination. The binding between bis(amino amides) and N-protected dicarboxylic amino acids has been thoroughly studied by ESI-MS and NMR spectroscopic methods as well as by molecular modeling.

C2 symmetrical nickel complexes derived from α-amino amides as efficient catalysts for the enantioselective addition of dialkylzinc reagents to aldehydes

A series of C2 symmetrical 1:2 Ni:L complexes derived from α-amino amides were studied for the enantioselective addition of dialkylzinc reagents to aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Through optimization of structure and reaction conditions, the best ligand provided secondary alcohols in excellent yields (up to 98%) and enantioselectivity of up to 99% ee for (R)-enantiomer. A transition state model has been proposed to explain the observed enantioselectivities based on computational calculations at the DFT level. Very interestingly, calculations suggest a coordination model of the aldehyde to the metal complex through association of a lone pair of the carbonyl oxygen to the hydrogen atom of an amino group.

Amino acid based low-molecular-weight tris(bis-amido) organogelators

Two new amino acid based low-molecular-mass organic gelators were designed, synthesized, and examined for their ability to gelate various organic solvents. The gelator molecules were found to aggregate via N-H...O hydrogen bonding to form an interwinding 3D network which immobilized a large number of organic solvents. Among the different organic solvents used in the gelation study mesitylene is found to be the best solvent. The microstructure of organogels was studied with FESEM and optical micrographs. The involvement of hydrogen bonding in the aggregation of the gelator molecule was studied using temperature dependent 1H NMR. The obtained organogels were found to exhibit significant mechanical strength.