25126-32-3 Usage
Originator
Kinevac,Squibb,US,1976
Uses
Sincalide is used in the biological studies in the preparation of opioid receptors agonistic and CCK receptor antagonistic activity.
Manufacturing Process
The starting material in the following synthesis is: t-butyloxycarbonyl-Laspartyl-
L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-Lphenylalanine
amide designated (SM).(A) A solution of (SM) (320 mg) in trifluoroacetic acid (7 ml) was kept under
nitrogen at room temperature for 15 minutes. Ether (100 ml) was added and
the precipitate filtered, washed thoroughly with ether and dried. This material
(280 mg) was added to concentrated sulfuric acid (20 ml), cooled at -20°C.
The solution was kept in the dry ice-acetone bath at -20°C for 75 minutes.
The sulfuric acid solution was poured into ice water (80 ml). The precipitate
was centrifuged, resuspended in ice water (30 ml) and 4N sodium hydroxide
was added until a clear solution was obtained. After reacidification to pH 4
with dilute sulfuric acid, the precipitate formed was centrifuged, washed twice
with ice water and dried. Yield 155 mg. Chromatograph of DEAE Sephadex
(with ammonium carbonate buffer) yielded the desired octapeptide sulfate
ester: 30 mg.(B) A solution of (SM) (330 mg) in trifluoroacetic acid (7 ml) was kept under
nitrogen at room temperature for 15 minutes. Ether (100 ml) was added and
the precipitate was filtered, washed thoroughly with ether and dried. This
material (300 mg) was added in portions to concentrated sulfuric acid (18 ml)
cooled at -20°C with vigorous stirring. After 15 minutes a solution of
potassium bisulfate in concentrated sulfuric acid (408 mg in 3 ml) was added.
The reaction mixture was stirred for 75 minutes at -15°C and then stored at -
7°C for 285 minutes. The sulfuric acid solution was poured into cold ether
(400 ml); precipitate was filtered, washed with cold ether, and suspended in
cold water. Complete solution was then achieved by careful addition of 2N
sodium hydroxide. Acidification with N hydrochloric acid led to the
precipitation of the desired octapeptide sulfate ester. Yield 200 mg.
Brand name
Kinevac (Bracco).
Therapeutic Function
Choleretic
General Description
It was thought originally that cholecystokinin and pancreozyminwere two different hormones. Cholecystokinin wasthought to be responsible for contraction of the gallbladder,whereas pancreozymin was believed to induce secretion ofpancreatic enzymes. It is now clear that both actions arecaused by a single 33-residue polypeptide, referred to ascholecystokinin–pancreozymin (CCK-PZ). CCK-PZ is secretedin the blood in response to the presence of food in theduodenum, especially long-chain fatty acids. The fiveCOOH-terminal amino acid residues are identical with thosein gastrin. The COOH-terminal octapeptide retains full activityof the parent hormone.
Biochem/physiol Actions
Neurotransmitter; predominant form of CCK in CNS and gastrointestinal tract; may play a role in satiety.
Check Digit Verification of cas no
The CAS Registry Mumber 25126-32-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,1,2 and 6 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 25126-32:
(7*2)+(6*5)+(5*1)+(4*2)+(3*6)+(2*3)+(1*2)=83
83 % 10 = 3
So 25126-32-3 is a valid CAS Registry Number.
InChI:InChI=1/C49H62N10O16S3/c1-76-18-16-34(55-47(69)37(58-44(66)32(50)23-41(61)62)21-28-12-14-30(15-13-28)75-78(72,73)74)45(67)53-26-40(60)54-38(22-29-25-52-33-11-7-6-10-31(29)33)48(70)56-35(17-19-77-2)46(68)59-39(24-42(63)64)49(71)57-36(43(51)65)20-27-8-4-3-5-9-27/h3-15,25,32,34-39,52H,16-24,26,50H2,1-2H3,(H2,51,65)(H,53,67)(H,54,60)(H,55,69)(H,56,70)(H,57,71)(H,58,66)(H,59,68)(H,61,62)(H,63,64)(H,72,73,74)/t32-,34-,35-,36-,37-,38-,39-/m0/s1
25126-32-3Relevant articles and documents
Methods for the production of peptide derivatives
-
Page/Page column 26, (2010/11/25)
The invention relates to methods for the preparation of peptides which are a C-terminal amide derivatives by a combination of solid-phase synthesis and post assembly solution phase synthesis. The peptides which are a C-terminal amide derivatives are further converted to peptide acetates. The invention also relates to pure peptide acetates and to protected peptide precursors.
Solid-Phase Synthesis of Peptide Amides on a Polystyrene Support Using Fluorenylmethoxycarbonyl Protecting Groups
Penke, Botond,Rivier, Jean
, p. 1197 - 1200 (2007/10/02)
We have investigated new routes for the synthesis of acid-sensitive amino acids using N-fluorenylmethoxycarbonyl amino acids and mild acid labile side chain protection in order to avoid HF cleavage as final step.The 4-(benzyloxy)benzylamine resin, applied successfully by Pietta and Brenna, proved to be unsuitable for the synthesis of peptide amides since we have found that trifluoroacetic acid treatment of peptide-resins yield the peptide still bearing a p-hydroxybenzyl group on the carboxamide nitrogen.We have successfully used the 2,4-dimethoxybenzhydrylamine support for the synthesis of peptide amides.Cholecystokinin octapeptide and GnRH were synthesized on the 2,4-dimethoxybenzhydrylamine resin and cleaved from the polymer with trifluoroacetic acid-thioanisole (4:1), and 95percent trifluroacetic acid containing phenol (2.5percent) and dimethyl sulfide (2.5percent), respectively.The final cleavage conditions had to be optimized in order to obtain good yields, suggesting that side chain protections of certain amino acids, possibly arginine and tryptophan, may have to be further refined.
