23828-09-3

Basic information

• Product Name: Z-PHE-SER-OME
• Synonyms: Z-PHE-SER-OME;(S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-hydroxypropanoate
• CAS NO: 23828-09-3
• Molecular Formula: C₂₁H₂₄N₂O₆
• Molecular Weight: 400.43
• Mol File: 23828-09-3.mol

Chemical Properties

• Melting Point: 125 °C
• Boiling Point: 667.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.257±0.06 g/cm3(Predicted)
• PKA: 11.06±0.46(Predicted)
• CAS DataBase Reference: Z-PHE-SER-OME(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PHE-SER-OME(23828-09-3)
• EPA Substance Registry System: Z-PHE-SER-OME(23828-09-3)

Safety Data

• Hazardous Substances Data: 23828-09-3(Hazardous Substances Data)

Upstream product

• 2788-84-3 (S)-serine methyl ester 
• 1161-13-3 N-Cbz-L-Phe 
• 77511-13-8 Z-Phe-O(TBA) 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 
• 3588-57-6 Z-DL-Phe-OH 
• 4865-47-8 phenyl ester of N-benzyloxycarbonyl-L-phenylalanine 

Downstream Products

• 5183-92-6 Z-Phe-D-Ser-NHNH₂ 
• 872130-35-3 N-benzyloxycarbonyl-L-phenylalanyl-DL-α-acetoxyglycine methyl ester 
• 16689-19-3 Z-L-Phe-Ser-NHNH₂ 
• 126749-79-9 Z-L-Phe-ΔAla-OMe 
• 16874-59-2 L-phenylalanyl-L-serine methyl ester hydrochloride 
• 368424-85-5 Phenylalanylserine methyl ester 
• 57287-86-2 cyclo(Ser-Phe) 
• 82155-27-9 (S)-3-tert-Butoxycarbonylamino-N-[(S)-1-((S)-2-hydroxy-1-methoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethyl]-succinamic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 94776-32-6 1-N--β-D-glucopyranosylamine 
• 82155-28-0 2-acetamido-1-N--2-deoxy-β-D-glucopyranosylamine 
• 82155-32-6 1-N--4-O-(β-D-glucopyranosyl)-β-D-glucopyranosylamine 
• 82168-80-7 N-(tert-butoxycarbonyl)-L-aspartyl-L-phenylalanyl-L-serine methyl ester 
• 82155-26-8 -L-phenylalanyl-L-serine methyl ester 
• 135112-29-7 Z-Arg(NO₂)-Pro-5-Ava-Phe-Ser(Ac)-Pro-Phe-Arg(NO₂)-OMe 

Relevant articles and documents

Phosphorus pentoxide for amide and peptide bond formation with minimal by-products

Phosphorus pentoxide and DMAP are used for amide bond formation from carboxylic acids and amines. Dipeptides and amides have been synthesized using this reagent in 42–77% yields and >99% ees. The protocol is attractive as it occurs at ambient temperature, the formation of organic by-products is minimal and the reagent can be readily quenched using water. Furthermore, excellent enantioselectivities are observed without the use of harsh triazole based additives.

Practical Peptide Synthesis Mediated by a Recyclable Hypervalent Iodine Reagent and Tris(4-methoxyphenyl)phosphine

6-(3,5-Bis(trifluoromethyl)phenyl)-1H,4H-2aλ3-ioda-2,3-dioxacyclopenta[hi]indene-1,4-dione (p-BTFP-iodosodilactone, 1a) was synthesized and demonstrated to be an efficient hypervalent iodine(III) reagent for the synthesis of dipeptides from various standard amino acids, including sterically hindered amino acids, in good to high yields within 30 min in the presence of tris(4-methoxyphenyl)phosphine. In addition, the combined system of 1a/(4-MeOC6H4)3P was used to synthesize the pentapeptide leu-enkephalin in protected form. It is worth noting that 1a can be regenerated readily after reaction.

Phenolic ester mediated oligopeptide synthesis promoted by HOBt

Although substituted phenolic ester mediated peptide synthesis is an efficient and well established method, the same via totally unsubstituted phenyl ester is not preferred due to the extremely slow rate of aminolysis. We have investigated the scope of the unsubstituted phenyl ester as an intermediate in peptide bond formation and found that it may be useful for the design of chemoselective peptide ligation when HOBt is used as an acyl transfer catalyst. The scope of HOBt catalyzed, oxo ester mediated ligation is explored for the synthesis of oligopeptides containing a cysteine, serine and threonine at the N-terminus of the ligating peptide.

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

BENZOTRIAZOL-1-YL DIETHYL PHOSPHATE. A NEW CONVENIENT COUPLING REAGENT FOR THE SYNTHESIS OF AMIDES AND PEPTIDES.

Benzotriazol-1-yl diethyl phosphate is found to be a new convenient coupling reagent for the synthesis of amides and practically racemization-free peptides.

SYNTHESIS OF 2-ACETAMIDO-1-N--2-DEOXY-β-D-GLUCOPYRANOSYLAMINE AND ANALOGS

2-Acetamido-1-N--2-deoxy-β-D-glucopyranosylamine and analogs containing D-glucopyranosyl, 4-O-β-D-glucopyranosyl-D-glucopyranosyl, L-Phe-L-Ala, and D-Phe-L-Ser were synth

Le chloroformiate d'isopropenyle (IPCF) en chimie des peptides. I. Un bon reactif pour le couplage peptidique : synthese de dipeptides modeles

Isopropenyl chloroformate was used as an activating agent of N-protected amino-acids in the mixed anhydride method.This new reagent allows to run mixed anhydrides couplings at room temperature.

ONE-POT CYCLIZATION OF A PEPTIDE BY THE USE OF (5-NITROPYRIDYL)DIPHENYL PHOSPHINATE: THE SYNTHESIS OF CYCLIC DECAPEPTIDE GRAMICIDIN S

One-pot synthesis of gramicidin S, cyclic decapeptide, was successfully achieved by treatment of the corresponding linear decapeptide with (5-nitropyridyl)diphenyl phosphinate, a new condensing reagent, in pyridine.Similarly, the phosphinic ester can be successfully employed in the Young test as well as syntheses of dipeptides.

15N NMR Spectroscopy. 30 - Structure/Shift Relationships of Oligopeptides and Copolypeptides, Including Gramicidin S.

The 15N NMR spectra of various oligopeptide derivatives of the Z-X-Y-Y-OMe structure, where X and Y are variable amino acids and Z is the benzyloxycarbonyl group, were measured in several protic and aprotic solvents.The shift difference of the 15N of the