7421-84-3

Usage

Uses

Used in Food and Beverage Industry:
Aspartame is used as a low-calorie sweetener for its high sweetness potency, allowing for a minimal amount to be used in comparison to sugar. This makes it suitable for products aimed at reducing calorie intake or catering to individuals with dietary restrictions, such as diabetes.
Used in Pharmaceutical Industry:
Aspartame is utilized as a sweetening agent in sugar-free medications and oral health products, providing a sweet taste without the calories or potential impact on blood glucose levels.
Used in Dietary Supplements:
Aspartame serves as a sweetening component in dietary supplements, particularly those designed for weight management or sugar reduction, offering an alternative to sugar without compromising taste.

InChI:InChI=1/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1

Upstream product

• 4976-94-7 Boc-Asp(OtBu)-Phe-OMe 
• 5262-07-7 Z-Asp(OBzl)-Phe-OMe 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 131021-87-9 <(4S)-2,2-bis(trifluoromethyl)-5-oxo-1,3-oxazolidine-4-yl>acetate 
• 33605-72-0 N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 77217-04-0 L-aspartic acid N-thiocarboxyanhydride 
• 40944-73-8 methyl ester of N-tert-butyloxycarbonyl-L-aspartyl-L-phenylalanine 
• 27446-39-5 N-[N-[(phenylmethoxy)carbonyl]-L-α-aspartyl]-L-phenylalanine 4-(1,1-dimethylethyl) 1-methyl ester 
• 125507-05-3 (S)-2-[(2-Benzyl-5-oxo-isoxazolidine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester 
• 101623-22-7 N-phenacetyl-α-L-aspartyl-L-phenylalanine methyl ester 
• 125507-07-5 (S)-2-{[(S)-5-Oxo-2-((R)-1-phenyl-ethyl)-isoxazolidine-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester 
• 140233-83-6 (S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-(2-p-tolyl-acetylamino)-succinamic acid 
• 140233-84-7 (S)-N-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-[2-(4-methoxy-phenyl)-acetylamino]-succinamic acid 

Downstream Products

• 3357-42-4 3-phenyl-1,2,4-triazole 
• 1418011-57-0 C₃₂H₅₂N₂O₆ 
• 1418011-58-1 C₃₂H₅₂N₂O₆ 
• 142955-73-5 3-Hydroxy-N-((S)-1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid 
• 142955-73-5 3-Hydroxy-N-((S)-1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid 
• 1307893-28-2 N-(N'-hex-5-ynoyl-L-α-aspartyl)-L-phenylalanine 1-methyl ester 
• 3618-96-0 (S)-N-acetylphenylalanine 
• 67-56-1 methanol 
• 55102-13-1 3-benzyl-6-carboxymethyl-2,5-diketopiperazine 

Relevant academic research and scientific papers

Synthesis of β-lactam peptidomimetics through Ugi MCR: First application of chiral Nβ-Fmoc amino alkyl isonitriles in MCRs

Chiral Nβ-Fmoc amino alkyl isonitriles were employed in Ugi multi component reactions (Ugi 4C-3CR) to obtain functionalized β-lactam peptidomimetics with l-aspartic acid α-methyl ester/peptide ester and organic aldehydes. The reactions were carried out in MeOH. Thirteen Ugi products have been prepared in good to moderate yields with good diastereoselectivities.

METHOD FOR THE SYNTHESIS OF PEPTIDES WITHOUT SOLVENT

The disclosure relates to a method for the synthesis of a compound of the formula (I) in which: n is an integer higher than or equal to 1; Rb and each Rn are independently a hydrogen atom, a C1-C6 arylalkyl group or a C1-C6 alkyl group substituted or not by an aryl group, —COOH, C1-C6, —COO-(alkyl), —CONH2, —SH, heteroaryl, —NH2, —NHC(NH)(NH2), C1-C6-s-(alkyl), —OH or phenol; Ra is a N-protective group; Rc is a ORd group in which Rd is a C1-C6 alkyl group or a NReRf group in which Re and Rf Re independently an N-protective group.

Solvent-free synthesis of peptides

Chamical Equation Presentation A crush on sweetness! The coupling of a urethane-protected N-carboxyanhydride of an amino acid with another amino acid derivative under ball-milling conditions gives a protected dipeptide in very high yield (see scheme; PG: protecting group). The reaction takes place in the solid state. The synthesis was applied to the preparation of a tri peptide and the sweetener aspartame, without any organic solvent or purification.

Hexafluoroacetone as protection and activation reagent in amino acid and peptide chemistry regiospecific α-functionalization of aspartic acid

A highly efficient method for regiospecific α-functionalization of aspartic acid is described. Key step is the synthesis of a N-protected and regioselectively α-carboxy-activated heterocyclic intermediate from aspartic acid and hexafluoroacetone. The new strategy offers i.a. a two step access to the sweetener Aspartame and to libraries of aspartame analogues.

Investigation of solid-state reactions using variable temperature X-ray powder diffractrometry. I. Aspartame hemihydrate

Purpose. The object of this study was to demonstrate the applicability of variable temperature X-ray powder diffractometry (XRD) to investigate solid-state reactions using aspartame as a model compound. Methods. Aspartame exists as a hemihydrate (ASH) under ambient conditions and converts to aspartame anhydrate (ASA) at ～130°C. ASA on further heating to ～180°C undergoes decomposition (intramolecular cyclization) to form a diketopiperazine derivative (DKP). The dehydration as well as the decomposition kinetics were studied isothermally at several temperatures. The unique feature of this technique is that it permits simultaneous quantification of the reactant as well as the product. Results. While the dehydration of ASH appeared to follow first-order kinetics, the cyclization of ASA was a nucleation controlled process. The rate constants were obtained at various temperatures, which permitted the calculation of the activation energies of dehydration and cyclization from the Arrhenius plots. The activation energy of dehydration was also calculated according to the method described by Ng (Aust. J. Chem., 28:1169-1178, 1975) and the two values were in good agreement. Conclusions. The study demonstrates that XRD is an excellent complement to thermal analysis and provides direct information about the solid-states of various reaction phases.

Process for preparing peptides and N-carbamoyl-protected peptides

The invention concerns a process for the enzymatic preparation of protected di- and oligopeptides and the separation of the protective groups used. The process according to the invention enables peptides to be synthesized simply and economically and the protective group to be separated carefully. The process comprises three reaction steps: 1. Preparation of N-carbamoyl amino acid or N-carbamoyl amino acid derivatives; 2. Formation of the peptide bond between the carbamoyl-protected electrophile and nucelophile; and 3. Separation of the carbamoyl-protective group.

Molecularly imprinted polymeric adsorbents for byproduct removal

In this study, both diastereo- and enantioselective adsorbents for a dipeptide derivative were prepared using a molecular imprinting technique. The diastereo- and enantioisomers for the dipeptide derivative N-(benzyloxycarbonyl)aspartylphenylalanine methyl ester (ZAPM), in addition to the α- and β-isomers, were chosen as test compounds for the investigation of the imprinting effect. The close similarities between the structures of different isomers make it possible to interpret the roles of template structure on specific molecular recognition. A highly specific byproduct scavenger was prepared by simultaneously incorporating methacrylic acid and vinylpyridine as functional monomers. The binding selectivities of polymeric adsorbents for the α- and β-isomers are shown to be greatly enhanced by introducing enantiocomplementarities into the polymer matrixes. An anti-β-L,L-ZAPM polymer was applied in a solid-phase extraction protocol, for the purification of the product in the chemical synthesis of N-protected aspartame. Finally, polymer beads were also imprinted against β-L,L-ZAPM using suspension polymerization performed in perfluorocarbon fluid. The imprinted polymer beads displayed the same binding characteristics as the imprinted bulk polymer and can be envisaged for the use of product purification in chromatographic mode.

Immobilized thermolysin and synthesis of precursor of aspartame

The optimal condition of the thermolysin-catalysed condensation reaction of N-benzyloxycarbonyl-DL-aspartic acid (Z-DL-Asp) with DL-phenylalanine methyl ester (DL-Phe-OMe) giving N-benzyloxycarbonyl-L-aspartyl-L-phenylalanine methyl ester, the precursor of the synthetic sweetener (aspartame, APM) has been investigated.The immobilized thermolysins have been prepared using seven polymethacrylate derivatives as carrier by covalent coupling of the polymers with enzyme.Seven derivatives have been synthesized using methacrylic acid, p-hydroxybenzoic acid and thecorresponding activated amide or amine.The abilities of the immobilized thermolysis to catalyze the condensation reaction have been tested and 100percent yield has been obtained by using one of them.

Hexafluoroacetone as Protecting Group and Activating Reagent in Amino Acid and Peptide Chemistry, XI. A New Simple Preparative Access to 2,5-Dioxopiperazines and 2,5-Dioxomorpholines

2,5-Dioxopiperazines with symmetrical as well as unsymmetrical substituent pattern can be obtained via 2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-ones, and 2,5-dioxomorpholines via 2,2-bis(trifluoromethyl)-1,3-dioxolan-4-ones, respectively. Keywords: Hexafluoroacetone; α-Amino acids; α-Hydroxy acids; 2,2-Bis(trifluoromethyl)-1,3-oxazolidin-5-ones; 2,2-Bis(trifluoromethyl)-1,3-dioxolan-4-ones; 2,5-Dioxopiperazines; 2,5-Dioxomorpholines.

Porous pharmaceutical form and its preparation

New porous, unitary freeze-dried pharmaceutical form, of homogeneous appearance, consisting of: a) an inclusion compound comprising: one or optionally more active substances, a predetermined quantity of cyclodextrin, optionally an additive facilitating inclusion, b) at least one substance chosen from: diluents, binders; and c) optionally one or more additives.