16689-13-7

Upstream product

• 1161-13-3 N-Cbz-L-Phe 
• 1499-46-3 L-Histidine methyl ester 
• 7389-87-9 L-histidine methyl ester dihydrochloride 
• 1161-13-3 N-(Benzyloxycarbonyl)-L-phenylalanine 
• 7389-87-9 (S)-histidine methyl ester dihydrochloride 
• 3588-57-6 Z-DL-Phe-OH 
• 4467-54-3 l-histidine methyl ester dihydrochloride 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 

Downstream Products

• 56586-95-9 (3S,6S)-3-((1H-Imidazol-5-yl)methyl)-6-benzylpiperazine-2,5-dione 
• 76524-86-2 L-Phe-L-His-OMe 
• 72827-29-3 (S)-2-((S)-2-Amino-3-phenyl-propionylamino)-3-(1H-imidazol-4-yl)-propionic acid methyl ester; hydrochloride 
• 120609-80-5 (S)-2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-phenyl-propionylamino]-3-(1H-imidazol-4-yl)-propionic acid 
• 120609-53-2 Z-Gly-L-Phe-L-His-OMe 
• 56586-95-9 Cyclo(histidylphenylalanine) 
• 20806-38-6 N-(Benzyloxycarbonyl-L-phenylalanyl)-L-histidine 
• 18779-16-3 L-phenylalanyl-L-histidine methyl ester dihydrobromide 
• 20806-35-3 ZPheHisN₂H₃ 
• 109603-66-9 ZAsnLys(Boc)PheHisThrPheProOH*HCl 
• 66253-25-6 ZPheHisN₃ 
• 53438-59-8 HPheHisThrPheProOH 
• 109539-11-9 ZPheHisThrPheProOBzl 
• 133230-90-7 N-acetyl-L-phenylalanyl-L-histidine methyl ester 

Relevant academic research and scientific papers

Design, synthesis, and application of enantioselective coupling reagent with a traceless chiral auxiliary

(Chemical Equation Presented) Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure

Imidazole-containing peptides having immunomodulatory activity

Imidazole-containing peptide of the formula: STR1 wherein R1 is a branched alkyl group, a branched alkyloxy group or an aryl-substituted lower alkyloxy group, R2 and R4 are the same or different and each is hydrogen atom o

Thermodynamic and (1)H NMR Study of Proton Complex Formation of Histidine-containing Cyclodipeptides in Aqueous Solution

A thermodynamic and (1)H NMR study of proton complex formation in aqueous solution of some L-histidine-containing cyclic L-dipeptides has been carried out.The enthalpic and entropic changes associated with protonation of the cyclodipeptides, obtained by potentiometric and calorimetric measurements, together with the (1)H NMR data and NOESY experiments, enable the role played by non-covalent interactions in proton complex formation to be assessed.In addition, a comparison with c(Gly-His) permits the influence of side-chain residues on the conformation of protonated species to be observed.

Mechanism of Enantioselective Ester Cleavage by Histidine-Containing Dipeptides at a Micellar Interface

Chiral p-nitrophenyl esters derived from the amino acid phenylalanine are cleaved by histidine-containing dipeptides at a micellar interface.High enantioselectivities (up to kL/kD = 30.4 at 0 deg C) are observed.Both the substrates and the catalysts contain an alternating sequence of hydrophobic and hydrophilic groups.Due to the need for hydration of the hydrophilic groups, the hydrophobic groups cannot dissolve completely into the micellar hydrocarbon phase.The kinetic data suggest that the micellar interface is capable of discriminating between transition states that have different hydrophilic and hydrophobic properties.One of the diastereomeric transition states is characterized by a hydrogen bond between the amide CO group of the ester and an NH group of the histidine-containing dipeptide.Upon formation of this hydrogen bond these polar CO and NH groups lose their hydrophilicity which allows the transfer of the adjacent apolar groups to the micellar hydrocarbon phase.The other diastereomeric transition state cannot form this hydrogen bond and the hydrophobic groups remain hydrated.Consequently, the latter transition state is of higher energy.The kinetic data reveal that it is important to prevent steric hinderance between the reactants in order to allow the unhindered formation of the hydrogen bond.

The Cyclic Dipeptide cyclo as a Catalyst for Asymmetric Addition of Hydrogen Cyanide to Aldehydes

cyclo (cyclo, 1) catalyzes the addition of hydrogen cyanide to benzaldehyde in toluene at -20 deg C to afford (R)-mandelonitrile with enantiomeric excess of 97 percent in high yield. cyclo gives (S)-mandelonitrile. cyclo (1) exhibits a broad substrate specificity, and a variety of aldehydes (3a-r) such as m-methoxybenzaldehyde (3c), 6-methoxy-2-naphthaldehyde (3k), and isobutyraldehyde (3o) similarly afforded the corresponding cyanohydrins with high enantiopurities (97 percent ee for 3c, 93 percent ee for 3k, 71 percent ee for 3o). (R)-Mandelonitrile thus obtained was successfully converted to various chiral synthons such as mandelic acid (7), methyl mandelate (8), and 2-amino-1-phenylethanol (9) without any racemization.

Cyclo-((S)-leucyl-(S)-histidyl). A Catalyst for Asymmetric Addition of Hydrogen Cyanide to Aldehydes

Asymmetric addition of hydrogen cyanide to various aldehydes in the presence of a catalytic amount of cyclo-((S)-leucyl-(S)-histidyl) affords the corresponding cyanohydrins in moderate to good optical yields.The reaction of benzaldehyde with hydrogen cyanide gives (S)-2-hydroxy-2-phenylacetonitrile (85percent, 55percent ee) whose stereochemistry is found to be opposite to our previous result using cyclo-((S)-phenylalanyl-(S)-histidyl).

SYNTHESIS OF A HEPTAPEPTIDE WITH SEQUENCE 17 - 23 OF HUMAN CALCITONIN

Two schemes for the synthesis of a peptide with sequence 17 - 23 of human calcitonin with the minimum protection of the lateral functions of the amino acids are proposed.