41518-17-6

Basic information

• Product Name: Z-Phe-O-COO-isoBu
• Synonyms: Z-Phe-O-COO-isoBu
• CAS NO: 41518-17-6
• Molecular Weight: 399.444
• Mol File: 41518-17-6.mol

Chemical Properties

• CAS DataBase Reference: Z-Phe-O-COO-isoBu(CAS DataBase Reference)
• NIST Chemistry Reference: Z-Phe-O-COO-isoBu(41518-17-6)
• EPA Substance Registry System: Z-Phe-O-COO-isoBu(41518-17-6)

Safety Data

• Hazardous Substances Data: 41518-17-6(Hazardous Substances Data)

Upstream product

• 1161-13-3 N-Cbz-L-Phe 
• 543-27-1 isobutyl chloroformate 
• 2448-45-5 Cbz-D-Phe 
• 3588-57-6 Z-DL-Phe-OH 
• 501-53-1 benzyl chloroformate 
• 673-06-3 D-(R)-phenylalanine 

Downstream Products

• 15196-02-8 (S)-3-[(benzyloxycarbonyl)amino]-1-diazo-4-phenyl-2-butanone 
• 148528-71-6 N-carbobenzyloxy-D-phenylalanine isopentylamide 
• 98714-71-7 methyl 2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropanoyl)amino]-2-methylpropanoate 
• 141345-69-9 Z-Phe-MeA-MeA-MeA-OBu^t 
• 6372-14-1 N-((benzyloxy)carbonyl)-L-phenylalaninol 
• 128719-79-9 N-benzyloxycarbonyl-D-phenylalanyl-N^α-methyl-L-lysyl(N^ε-Me,Boc)-D-tryptophyl-L-leucine methyl ester 
• 58917-85-4 N-(benzyloxycarbonyl)-D-phenylalaninol 
• 16856-21-6 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-(1H-indol-3-yl)propanoate 
• 109003-53-4 Z-Phe-Gly-Leu-Met-NH₂ 
• 70328-25-5 Z-Phe-Phe-Gly-Leu-Met-NH₂ 
• 120452-49-5 N-methoxy-N-methyl-(R)-N²-Cbz-phenylalaninamide 
• 63655-58-3 Z-D-Phe-Ser-OMe 
• 28426-51-9 methyl ((benzyloxy)carbonyl)-L-phenylalanyl-L-prolinate 
• 26049-94-5 (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate 

Relevant articles and documents

Ecological base-conditioned preparation of dipeptides using unprotected α-amino acids containing hydrophilic side chains

The coupling reactions of 3-phenylpropanoic acid and Ncarboxybenzyl á-amino acids with unprotected á-amino acids containing hydrophilic side chains such as aliphatic alcohol, aromatic alcohol, thiol, carboxylic acid, and amide afforded the corresponding amides in 6696% yield without racemization via the corresponding mixed carbonic carboxylic anhydrides under basic conditions through an ecological green synthetic method.

α-N-Protected dipeptide acids: A simple and efficient synthesis via the easily accessible mixed anhydride method using free amino acids in DMSO and tetrabutylammonium hydroxide

The importance of dipeptides both in medicinal and pharmacological fields is well documented and many efforts have been made to find simple and efficient methods for their synthesis. For this reason, we have investigated the synthesis of α-N-protected dipeptide acids by reacting the easily accessible mixed anhydride of α-N-protected amino acids with free amino acids under different reaction conditions. The combination of TBA-OH and DMSO has been found to be the best to overcome the low solubility of amino acids in organic solvents. Under these experimental conditions, the homogeneous phase condensation reaction occurs rapidly and without detectable epimerization. The present method is also applicable to side-chain unprotected Tyr, Trp, Glu, and Asp but not Lys. This latter residue is able to engage two molecules of mixed anhydride giving the corresponding isotripeptide. Moreover, the applicability of this protocol for the synthesis of tri- and tetrapeptides has been tested. This approach reduces the need for protecting groups, is cost effective, scalable, and yields dipeptide acids that can be used as building blocks in the synthesis of larger peptides.

Sodium borohydride reduction of carbamoyl azide function: A synthesis of N-protected N'-formyl-gem-diaminoalkyl derivatives

A simple, efficient two-step synthesis of N-protected N′-formyl-gem- diaminoalkyl derivatives is reported. The procedure involves the unprecedented reduction of the carbamoyl azide of α-N-Boc/Fmoc/Z-protected amino acids and dipeptides (Boc = tert-butoxycarbonyl, Fmoc = 9-fluorenylmethoxycarbonyl, Z = benzyloxycarbonyl) by treatment with NaBH4 at room temperature. The reaction proceeds rapidly (45 min) without detectable epimerization (by HPLC-ESI-MS analysis) and is not influenced by the nature of the starting carbamoyl azide. The 1H and 13C NMR analyses of the synthesized N-protected N′-formamides were carried out in [D 6]DMSO. The spectra exhibited the presence of two rotameric forms in solution as a result of the restricted rotation around the N-CO formyl bond. The integration of the N-CH-N protons of the two isomers showed that the cis isomer (rotamer B) was the more abundant conformer by 60 to 78 %. The reported synthesis represents the potential value of carbamoyl azides as versatile chiral starting materials for many synthetic purposes. A simple two-step synthesis of N-protected N′-formyl-gem-diaminoalkyl derivatives is reported that employs the reduction of the carbamoyl azide of N-protected amino acids and N-protected dipeptide acids with NaBH4. This racemization-free protocol is compatible with the most commonly used N-protecting groups. Copyright

Synthesis and characterization of chiral di(N-protected-α-amino) diazo-β-diketones from α-diazoketones and imidazolides derived from amino acids

Di(N-protected-α-amino)diazo-β-diketones were prepared by the reaction of activated N-protected-α-amino acids (imidazolides) with α-diazoketones, derived from natural amino acids, in the presence of lithium diisopropylamide in tetrahydrofuran as the solvent at -78 °C.

Primary amino acid derivatives: Compounds with anticonvulsant and neuropathic pain protection activities

Pharmacological management remains the primary method to treat epilepsy and neuropathic pain. We have advanced a novel class of anticonvulsants termed functionalized amino acids (FAAs). In this study, we examine FAA derivatives from which the terminal acetyl moiety was removed and termed these compounds primary amino acid derivatives (PAADs). Twenty-seven PAADs were prepared; the central C(2) R-substituent was varied, including C(2) stereochemistry, and the compounds were tested in rodent models of seizures and neuropathic pain. C(2)-Hydrocarbon N-benzylamide PAADs were potent anticonvulsants and excellent anticonvulsant activity (mice, ip; rat, po) was observed for C(2) R-substituted PAADs in which the R group was ethyl, isopropyl, or tert-butyl, and the C(2) stereochemistry conformed to the d-amino acid configuration ((R)-stereoisomer). These values surpassed the activities of several clinical antiepileptic drugs. The C(2) (R)-ethyl and C(2) (R)-isopropyl PAADs also displayed excellent activities in the mouse (ip) formalin neuropathic pain model. Significantly, unlike the FAA structure-activity relationship, PAAD anticonvulsant activity increased upon substitution of a methylene unit for a heteroatom in the R-substituent that was one atom removed from the C(2) site, suggesting that these PAADs function by a different pathway than FAAs.

Synthesis and biological evaluation of novel irreversible serine protease inhibitors using amino acid based sulfonyl fluorides as an electrophilic trap

We have designed and synthesized novel irreversible serine protease inhibitors containing aliphatic sulfonyl fluorides as an electrophilic trap. These substituted taurine sulfonyl fluorides derived from taurine or protected amino acids were conveniently s

Inhibitors of human neutrophil elastase based on a highly functionalized N-amino-4-imidazolidinone scaffold

A series of compounds based on the N-amino-4-imidazolidinone scaffold was synthesized and screened against human neutrophil elastase (HNE). These studies lead to the identification of a selective, low micromolar reversible competitive inhibitor of HNE. A series of derivatives based on the N-amino-4- imidazolidinone scaffold (I) was synthesized and shown to inhibit human neutrophil elastase.

Synthesis and applications of β-aminoethanesulfonyl azides

A very efficient method for the synthesis of β-aminoethanesulfonyl azides is descibed. These aliphatic sulfonyl azides are accessible starting from a variety of protected amino acids, including those having functionalized side chains. Furthermore, these s

Building functionalized peptidomimetics: Use of electroauxiliaries for introducing N-acyliminium ions into peptides

A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.

Asymmetric synthesis of substituted 1-aminocyclopropane1-carboxylic acids via diketopiperazine methodology

Diketopiperazinespirocyclopropane 12 is prepared in > 98% d.e. via the conjugate addition of a phosphorus ylide to (6S)-N, N′-bis(p-methoxybenzyl)-3-methylenepiperazine-2,5-dione 2. Deprotection and hydrolysis of adduct 12 and subsequent peptide coupling demonstrate the applicability of this methodology to the asymmetric synthesis of 1-aminocyclopropane-1-carboxylic acids for incorporation into novel peptides. A model for the high level of diastereofacial selectivity observed in the cyclopropanation reaction is presented. A highly selective asymmetric approach (> 98% d.e.) to (S)-[2,2-2H 2]-1-aminocyclopropane-l-carboxylic acid 29 is also reported via a deuterated sulfur ylide addition to acceptor 2.