1947-37-1

Basic information

• Product Name: TETRAGASTRIN
• Synonyms: (3S)-3-[[(1S)-1-carbamoyl-2-phenyl-ethyl]carbamoyl]-3-[[(2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-phenylmethoxycarbonylamino-propanoyl]amino]-4-methylsulfanyl-butanoyl]amino]propanoic acid;4-7-Cholecystokinin-7 (swine) (9CI);Alaninamide, L-tryptophyl-L-methionyl-L-aspartylphenyl- (7CI);Alaninamide, L-tryptophyl-L-methionyl-L-aspartylphenyl-, L- (8CI);Cholecystokinin C-terminal tetrapeptide;Cholecystokinin(36-39);L-Phenylalaninamide, L-tryptophyl-L-methionyl-L-a-aspartyl-;Cholecystokinin fragment 30-33 amide
• CAS NO: 1947-37-1
• Molecular Formula: C₂₉H₃₆N₆O₆S
• Molecular Weight: 730.83
• Mol File: 1947-37-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 185-195 °C
• Boiling Point: 1159.2°Cat760mmHg
• Flash Point: 654.8°C
• Appearance: /
• Density: 1.341g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: ?20°C
• PKA: 4.19±0.10(Predicted)
• CAS DataBase Reference: TETRAGASTRIN(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAGASTRIN(1947-37-1)
• EPA Substance Registry System: TETRAGASTRIN(1947-37-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1947-37-1(Hazardous Substances Data)

Usage

Description

TETRAGASTRIN, also known as Cholecystokinin Fragment 30-33 Amide, is a peptide derived from the cholecystokinin (CCK) hormone. It is a small fragment of the larger CCK molecule and possesses biological activity, making it a valuable compound for various applications in the pharmaceutical and medical fields.

Uses

Used in Pharmaceutical Research:
TETRAGASTRIN is used as an inactivator for the CCK8 antiserum, which is crucial in the development and testing of pharmaceuticals targeting the cholecystokinin system. By inactivating the antiserum, researchers can study the effects of CCK and its interactions with other biological molecules.
Used in Diagnostic Applications:
In the field of diagnostics, TETRAGASTRIN serves as an antigen used in absorption control for testing the specificity of antisera. This application is essential for validating the accuracy and reliability of diagnostic tests that target the cholecystokinin system, ensuring that they are specific to the intended biological markers.
Used in Medical Research:
TETRAGASTRIN is also utilized in medical research to study the role of cholecystokinin in various physiological processes and diseases. By understanding the interactions of this peptide with other molecules, researchers can develop new therapeutic strategies for conditions related to the cholecystokinin system, such as gastrointestinal disorders and certain types of cancer.

Hazard

Moderately toxic by ingestion

Biochem/physiol Actions

Cholecystokinin Fragment 30-33 Amide also referred to as CCK-4 or Trp-Met-Asp-Phe amide is a peptide fragment derived from peptide hormone cholecystokinin. CCK-4 is a panicogenic agent that induces panic attacks in humans. This property of the compound can be used in scientific research for testing the new anxiolytic drugs.

InChI:InChI=1/C29H36N6O6S/c1-42-12-11-22(33-27(39)20(30)14-18-16-32-21-10-6-5-9-19(18)21)28(40)35-24(15-25(36)37)29(41)34-23(26(31)38)13-17-7-3-2-4-8-17/h2-10,16,20,22-24,32H,11-15,30H2,1H3,(H2,31,38)(H,33,39)(H,34,41)(H,35,40)(H,36,37)/t20-,22-,23-,24-/m0/s1

Upstream product

• 5241-58-7 L-Phenylalanine amide 
• 97586-87-3 H-Trp-Met-Asp-OH 
• 86061-01-0 tert-butyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-pentafluorophenyl L-aspartate 
• 86069-87-6 N-α-fluorenylmethoxycarbonyl-L-tryptophan pentafluorophenyl ester 
• 86060-92-6 N-α-Fmoc-L-phenylalanine pentafluorophenyl ester 
• 86060-94-8 N-α-Fmoc-L-methionine pentafluorophenyl ester 
• 110592-11-5 Boc-Trp(Mts)-Met-Asp(OMen)-Phe-NH₂ 
• 13139-14-5 Boc-Trp-OH 
• 15160-31-3 (tert-butyloxycarbonyl)-l-tryptophan p-nitrophenyl ester 
• 103802-00-2 Boc-Met-Asp-OH 
• 123197-15-9 Boc-Trp-Met-Asp-OH 
• 110575-50-3 (S)-3-tert-Butoxycarbonylamino-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 110575-51-4 Z(OMe)-Met(O)-Asp(OMen)-Phe-NH₂ 
• 110575-52-5 Boc-Trp(Mts)-Met(O)-Asp(OMen)-Phe-NH₂ 

Downstream Products

• 1032744-64-1 1-chloromethyl-5-hydroxy-3-(5,6,7-trimethoxyindole-2-carbonyl)-2,3-dihydro-1H-benz[e]indole-7-carboxylic acid [β-alanyl-L-tryptophyl-L-methionyl-L-aspartyl-L-phenylalanineamidyl] amide 
• 21438-63-1 Trp-Met 
• 97586-87-3 H-Trp-Met-Asp-OH 

Relevant articles and documents

Enzymatic C-terminal amidation of amino acids and peptides

Herein, we describe two versatile and high yielding enzymatic approaches for the conversion of semi-protected amino acid and peptidyl C-terminal α-carboxylic acids into their corresponding amides. In the first approach, the lipase Candida antarctica lipase-B (Cal-B), and in the second approach, the protease Subtilisin A, are used, respectively. We found that by using the ammonium salt of the α-carboxylic acid instead of separate ammonia sources, the enzymatic amidation reactions proceeded much faster without side reactions and gave near to quantitative yields of products.

A Modified Benzhydrylamine as a Handle Reagent for the Solid Phase Synthesis of Peptide Amides Based on the Fluorenylmethoxycarbonyl Method

An easily preparable dimethoxybenzhydrylamine derivative, 3-(α-Fmoc-amino-4-methoxybenzyl)-4-methoxyphenyl propionic acid (Fmoc=fluoren-9-ylmethoxycarbonyl) is a useful precursor of the C-terminal amide, when applied to Fmoc-based solid phase peptide synthesis; as a cleavage reagent from the resine, thioanisole-mediated trimethylsilyl bromide in trifluoroacetic acid is recommended.

Alternative Synthesis of the Carboxyl Terminal Tetrapeptide Amide of Cholecystokinin by Means of Proteases

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