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(S)-2-amino-3-(tritylmercapto)propionic acid methyl ester, also known as (S)-ATMPA methyl ester, is a compound with a molecular formula of C21H21NO2S. It is a derivative of the amino acid cysteine and comprises a trityl-protected thiol group. (S)-2-amino-3-(tritylmercapto)propionic acid methyl ester is characterized by its unique structure, which makes it a versatile building block in organic synthesis and a promising candidate in the field of medicinal chemistry.

115545-85-2

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115545-85-2 Usage

Uses

Used in Organic Synthesis:
(S)-2-amino-3-(tritylmercapto)propionic acid methyl ester is used as a building block for the preparation of various bioactive molecules. Its unique structure allows for the creation of a wide range of compounds with potential applications in different industries.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-2-amino-3-(tritylmercapto)propionic acid methyl ester is used as a key component in the development of new pharmaceuticals. Its trityl-protected thiol group provides a valuable starting point for the synthesis of novel therapeutic agents.
Used in Protein Structure and Function Studies:
(S)-2-amino-3-(tritylmercapto)propionic acid methyl ester is used as a valuable tool in the study of protein structure and function. Its trityl-protected thiol group enables researchers to investigate the roles of cysteine residues in proteins and their interactions with other biomolecules.
Used in Bioconjugate Development for Targeted Drug Delivery:
In the development of new bioconjugates for targeted drug delivery, (S)-2-amino-3-(tritylmercapto)propionic acid methyl ester is used as a key component. Its trityl-protected thiol group facilitates the attachment of drug molecules to targeting ligands, enhancing the specificity and efficacy of drug delivery systems.

Check Digit Verification of cas no

The CAS Registry Mumber 115545-85-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,5,5,4 and 5 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 115545-85:
(8*1)+(7*1)+(6*5)+(5*5)+(4*4)+(3*5)+(2*8)+(1*5)=122
122 % 10 = 2
So 115545-85-2 is a valid CAS Registry Number.

115545-85-2Relevant articles and documents

Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles

Vishwanatha, Thimmalapura M.,Kurpiewska, Katarzyna,Kalinowska-Tlu?cik, Justyna,D?mling, Alexander

, p. 9585 - 9594 (2017)

An alternative approach toward the simple and robust synthesis of highly substituted peptidic thiazole derivatives using Ugi-multicomponent reaction (U-MCR) is described. Thus, we introduced the enantiopure (R)-2-methyl-2-isocyano-3-(tritylthio)propanoate as a novel class of isocyanide in MCR. This bifunctional isocyanide was found to undergo mild cyclodehydration to afford thiazole containing peptidomimetics in a short synthetic sequence. Several examples of bis-heterocyclic rings were also synthesized through the proper choice of the aldehyde component in the U-4CR. The method opens a wide range of applications toward the synthesis of nonribosomal natural products and other bioactive compounds.

Tubulysin Synthesis Featuring Stereoselective Catalysis and Highly Convergent Multicomponent Assembly

Vishwanatha, Thimmalapura M.,Giepmans, Ben,Goda, Sayed K.,D?mling, Alexander

, p. 5396 - 5400 (2020)

A concise and modular total synthesis of the highly potent N14-desacetoxytubulysin H (1) has been accomplished in 18 steps in an overall yield of up to 30percent. Our work highlights the complexity-augmenting and route-shortening power of diastereoselective multicomponent reaction (MCR) as well as the role of bulky ligands to perfectly control both the regioselective and diastereoselective synthesis of tubuphenylalanine in just two steps. The total synthesis not only provides an operationally simple and step economy but will also stimulate major advances in the development of new tubulysin analogues.

Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore

Miura, Chihiro,Kiyama, Masahiro,Iwano, Satoshi,Ito, Kazuto,Obata, Rika,Hirano, Takashi,Maki, Shojiro,Niwa, Haruki

, p. 9726 - 9734 (2013)

New firefly luciferin analogs of the 4,4′-substituted biphenyl-type were synthesized. One analog with a 4′-dimethylamino group possessed bioluminescence activity, emitting near-infrared biological window light at 675 nm suitable for deep-site bioimaging of living animals. The chemiluminescence light-emission maximum of the corresponding methyl ester of the bioluminescence active analog was 500 nm, implying that biphenyl and thiazolinone rings in the light emitter might be placed in a coplanar conformation at the polar luciferase active site.

Intramolecular hydrogen-bonding activation in cysteines: A new effective radical scavenger

Haya, Luisa,Osante, I?aki,Mainar, Ana M.,Cativiela, Carlos,Urieta, Jose S.

, p. 9407 - 9413 (2013)

The challenge of developing organic molecules with improved antioxidant activities for a competitive marketplace requires, given the great amount of possibilities, much laboratory work. Nowadays, the ability of methodologies based on quantum chemistry to determine the influence of different modifications on a molecule core provides a powerful tool for selecting the most useful derivatives to be synthesized. Here, we report the results of the assessment of antioxidant activity for quaternary amino acids, specifically for cysteine derivatives. The effect of introducing different substituents on the cysteine core is evaluated by using DFT to obtain an adequate structure-antioxidant activity relationship. This theoretical study shows a small panel of targets among which (R)-N-acetyl-2-methylcysteine methyl ester 15 exhibits special features and relevant antioxidant activity. The conformational 1H NMR study of this synthesized compound indicates the existence of an intramolecular C7 member ring involving S-H?OC substructure, which is reported for the first time in the literature for this amino acid unit. This unusual conformation seems to be the reason for the high antioxidant capacity experimentally found for this compound.

Synthesis and stereochemistry of (?)-FE399

Ishigami, Ken,Katsuta, Ryo,Kimura, Kenji,Masada, Naoko,Nukada, Tomoo,Yajima, Arata

, (2020)

The stereochemistry of selective anticancer compound FE399 was determined to be rel-9R,14R,17R by theoretical and synthetic studies. Relative stereochemistry of FE399 was predicted by comparison of the 13C NMR chemical shifts of the natural sample with that predicted by theoretical calculation for each possible stereoisomer. The first synthesis of (9R,14R,17R)-(?)-FE399 was achieved using an amide formation of a dithiazocane with a hydroxy dodecanoic acid derivatives and sixteen-membered macrolactonization as key steps. The overall yield was 18% in ten steps from L-cysteine and (S)-glycidyl tosylate.

Oxidative peptide bond formation of glycine-amino acid using 2-(aminomethyl)malononitrile as a glycine unit

Wang, Xiaoling,Li, Jing,Hayashi, Yujiro

supporting information, p. 4283 - 4286 (2021/05/05)

Amide linkage of glycine-amino acid was synthesized by coupling of substituted 2-(aminomethyl)malononitrile as a C-terminal glycine unit and N-terminal amine using CsOAc and O2in an aqueous solution. This is a coupling reagent-free and catalyst-free peptide synthesisviaoxidative amide bond formation. Various tripeptides and tetrapeptides were synthesized efficiently and the sulfide moiety is inert even under an oxygen atmosphere.

Structurally Diverse Acyl Bicyclobutanes: Valuable Strained Electrophiles

Attard, Riley H.,Gardiner, Michael G.,Malins, Lara R.,Schwartz, Brett D.,Zhang, Meng Yao

, p. 2808 - 2812 (2020/03/04)

Bicyclo[1.1.0]butanes (BCBs) are highly strained carbocycles that have emerged as versatile synthetic tools, particularly for the construction of functionalized small molecules. This work reports two efficient pathways for the rapid preparation of over 20 structurally diverse BCB ketones, encompassing simple alkyl and aryl derivatives, as well as unprecedented amino acid, dipeptide, bioisostere, and bifunctional linchpin reagents currently inaccessible using literature methods. Analogues are readily forged in two steps and in high yields from simple carboxylic acids or through unsymmetrical ketone synthesis beginning with a convenient carbonyl dication equivalent. The utility of this novel toolbox of strained electrophiles for the selective modification of proteinogenic nucleophiles is highlighted.

TUBULYSIN DERIVATIVES AND METHODS FOR PREPARING THE SAME

-

Page/Page column 26; 27, (2020/02/16)

The invention relates to novel means and methods for the synthesis of tubulysin and derivatives thereof, which find their use e.g. as cytotoxic agents in targeted drug delivery. Provided is a method for preparing a tubulysin derivative, comprising reacting compounds A, B and C in a 3- component Passerini reaction, wherein compound A is a carboxylic acid according to the general formula (A); wherein compound B is an aldehyde according to the general formula (B); and wherein compound C is an isocyanide according to the general formula (C).

Method for synthesizing impurity isomers of bupropion hydrochloride sustained-release tablets and application of impurity isomers

-

Paragraph 0055, (2017/11/01)

The invention discloses a method for synthesizing impurity enantiomers of bupropion hydrochloride, and belongs to the field of pharmaceutical and chemical engineering. The method includes carrying out mercapto protection, condensation and de-protection cyclization consecutive reaction on D-cysteine methyl ester hydrochloride (a compound I) which is used as a starting material; separating and hydrolyzing isomers by means of column chromatography to obtain (3S, 5S, 6S)-6-(3-chlorphenyl)-6-hydroxyl-5-methyl thiomorpholine-3-carboxylic acid and (3S, 5R, 6R)-6-(3-chlorphenyl)-6-hydroxyl-5-methyl thiomorpholine-3-carboxylic acid. The method has the advantages of concise and efficient synthetic route, stereospecific chiral control, high reaction yield and inexpensive and easily available materials, solvents and reagents. Besides, the impurity enantiomers can be used for controlling the quality of bupropion hydrochloride sustained-release tablets or can be used as impurity reference substances.

Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics

Vishwanatha, Thimmalapura M.,Bergamaschi, Enrico,D?mling, Alexander

supporting information, p. 3195 - 3198 (2017/06/23)

A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.

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