52574-08-0

Basic information

• Product Name: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID
• Synonyms: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID;S-ACETAMIDOMETHYL-DEAMINO-CYSTEINE;S-(ACETYL-AMINOMETHYL)-3-MERCAPTOPROPIONIC ACID;MPA(ACM)-OH;(ACM)SCH2CH2COOH;3-(ACETYLAMINOMETHYLSULFANYL)PROPIONIC ACID;3-(ACETAMIDO-METHYLSULFANYL)-PROPIONIC ACID;3-MERCAPTOPROPIONIC ACID(ACM)
• CAS NO: 52574-08-0
• Molecular Formula: C₆H₁₁NO₃S
• Molecular Weight: 177.22
• Product Categories: Other Reagents
• Mol File: 52574-08-0.mol

Chemical Properties

• Melting Point: 240C
• Boiling Point: 430.1±30.0 °C(Predicted)
• Appearance: /
• Density: 1.247±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.31±0.10(Predicted)
• CAS DataBase Reference: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID(52574-08-0)
• EPA Substance Registry System: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID(52574-08-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-36
• Safety Statements: 26-36
• Hazardous Substances Data: 52574-08-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Synthetic route

N-(hydroxymethyl)acetamide (625-51-4) + 3-mercaptopropionic acid (107-96-0) → 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0)

Conditions	Yield
In trifluoroacetic acid for 0.5h; Ambient temperature;	62%

3-(tritylthio) propanoic acid (27144-18-9) + N-(hydroxymethyl)acetamide (625-51-4) → 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0)

Conditions	Yield
With trifluoroacetic acid for 2.5h;	17.1%

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + methyl (S)-7-amino-3{[(tert-butoxy)carbonyl]amino}heptanoate → methyl (S)-7-({3-[(acetylamino)methylsulfanyl]propionyl}amino)-3-{[(tert-butoxy)carbonyl]amino}haptanoate (329348-46-1)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In chloroform at 0 - 20℃; for 23h;	92%

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + Z-Gly-Glu(O-But)-Arg(Adoc)2-OH (86095-68-3) → Acm-SCH2.CH2CO.Gly.Glu.(OBut).Arg(Adoc)2OH (86095-70-7)

Conditions	Yield
With 4-methyl-morpholine; pivaloyl chloride In N,N-dimethyl-formamide for 2h;	59%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid (13850-91-4, 45170-31-8, 89536-85-6) → (S)-2-((R)-2-{[3-(Acetylamino-methylsulfanyl)-propionyl]-methyl-amino}-3-methyl-butyrylamino)-3-phenyl-propionic acid

Conditions	Yield
Multistep reaction;

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid (115962-35-1, 144069-68-1, 78879-20-6) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid (13850-91-4, 45170-31-8, 89536-85-6) → (S)-2-((R)-2-{[3-(Acetylamino-methylsulfanyl)-propionyl]-methyl-amino}-3-methyl-butyryl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

Conditions	Yield
Multistep reaction;

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + chloro(chlorosulfanyl)methanone (2757-23-5) + N-methylaniline (100-61-8) → S-[(N-methyl-N-phenylcarbamoyl)sulfenyl]-β-thiopropionic acid

Conditions	Yield
1.) CHCl3, 10 min, 2.) CHCl3, 20 min; Yield given. Multistep reaction;

(chlorocarbonyl)disulfanyl chloride (79341-73-4) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + N-methylaniline (100-61-8) → S-[(N-methyl-N-phenylcarbamoyl)disulfanyl]-β-thiopropionic acid

Conditions	Yield
1.) CHCl3, 10 min, 2.) CHCl3, 20 min; Yield given. Multistep reaction;

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + Arg-Val-Tyr-Val-His-Pro-Phe-OH-resin → [Mpr(S-Acm)(1)Val(5)]angiotensin II (184353-68-2)

Conditions	Yield
With hydrogen fluoride; benzotriazol-1-ol; dicyclohexyl-carbodiimide 1.) DMF/CH2Cl2; Multistep reaction;

N-Fmoc L-Phe (35661-40-6) + Fmoc-Trp-OH (35737-15-6) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-(2-((acetamidomethyl)thio)ethyl)glycine (425428-82-6) + Fmoc-D-Trp-OH + Fmoc-Lys-OH Fmoc-Thr(t-Bu)-OH → 2-[(7S,10S,13S,16R,19S,22S)-13-(4-Amino-butyl)-7,22-dibenzyl-10-((R)-1-hydroxy-ethyl)-16,19-bis-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24-heptaoxo-1,2-dithia-5,8,11,14,17,20,23-heptaaza-cyclohexacos-5-yl]-acetamide

Conditions	Yield
Multistep reaction.;

N-Fmoc L-Phe (35661-40-6) + Fmoc-Trp-OH (35737-15-6) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-(2-((acetamidomethyl)thio)ethyl)glycine (425428-82-6) + Fmoc-D-Trp-OH + Fmoc-Lys-OH Fmoc-Thr(t-Bu)-OH → 2-[(7S,10S,13S,16R,19S,22S,25R)-25-Amino-13-(4-amino-butyl)-7,22-dibenzyl-10-((R)-1-hydroxy-ethyl)-16,19-bis-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24-heptaoxo-1,2-dithia-5,8,11,14,17,20,23-heptaaza-cyclohexacos-5-yl]-acetamide

Conditions	Yield
Multistep reaction.;

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) → (S)-7-({3-[(acetylamino)methylsulfanyl]propionyl}amino)-3-{[(tert-butoxy)carbonyl]amino}haptanoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / Et3N; EDC; HOBt / CHCl3 / 23 h / 0 - 20 °C 2: 74 percent / aq. NaOH / methanol / 21.5 h View Scheme

Upstream product

• 27144-18-9 3-(tritylthio) propanoic acid 
• 625-51-4 N-(hydroxymethyl)acetamide 
• 107-96-0 3-mercaptopropionic acid 

Downstream Products

• 184353-68-2 [Mpr(S-Acm)⁽¹⁾Val⁽⁵⁾]angiotensin II 

Relevant articles and documents

NOVEL MULTIMERIC MOLECULES, A PROCESS FOR PREPARING THE SAME AND THE USE THEREOF FOR MANUFACTURING MEDICINAL DRUGS

The invention relates to a compound of the formula (I): in which k and j are independently 0 or 1, Y is a macrocycle in which the cycle includes 9 to 36 carbon atoms and is functionalised by three amino functions and by a chain for attaching the spacer arm Z via an X bond, Rc is a binding pattern with a receptor of the TNF superfamily, X is a chemical function for binding the Y group to the space arm, and Z is a bi-, tri- or tetra-functional spacer arm.

Human somatostatin receptor specificity of backbone-cyclic analogues containing novel sulfur building units

Somatostatin 14 (somatostatin) and its clinically available analogues octreotide, lanreotide, and vapreotide are potent inhibitors of growth hormone, insulin, and glucagon release. Recently, a novel backbone cyclic somatostatin analogue c(GABA-Phe-Trp-(D)Trp-Lys-Thr-Phe-GlyC3-NH2) (analogue 1, PTR 3173) that possesses in vivo endocrine selectivity was described. This long-acting octapeptide exhibits high affinity to human recombinant somatostatin receptors (hsst) hsst2, hsst4, and hsst5. Its novel binding profile resulted in potent in vivo inhibition of growth hormone but not of insulin release. We report the synthesis, bioactivity, and structure-activity relationship studies of compounds related to 1. In these analogues, the lactam bridge of 1 was replaced by a backbone disulfide bridge. We present a novel approach for conformational constraint of peptides by utilizing sulfur-containing building units for on-resin backbone cyclization. These disulfide backbone cyclic analogues of 1 showed significant metabolic stability as tested in various enzyme mixtures. Receptor binding assays revealed different receptor selectivity profiles for these analogues in comparison to their prototype. It was found that analogues of 1, bearing a disulfide bridge, had increased selectivity to hsst2 and hsst5; however, they exhibited weaker affinity to hsst4 as compared to 1. These studies imply that ring chemistry, ring size, and ring position of the peptide template may affect the receptor binding selectivity.