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Cas Database

72122-63-5

72122-63-5

Identification

  • Product Name:Glycine,L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolyl-

  • CAS Number: 72122-63-5

  • EINECS:230-640-8

  • Molecular Weight:579.653

  • Molecular Formula: C30H37 N5 O7

  • HS Code:

  • Mol File:72122-63-5.mol

Synonyms:Glycine,N-[1-[N-(1-L-tyrosyl-L-prolyl)-L-phenylalanyl]-L-prolyl]-; 16: PN: WO2005027953PAGE: 32 unclaimed sequence; 21: PN: WO2007025286 SEQID: 20 unclaimed sequence;27: PN: WO0210195 PAGE: 63 claimed sequence; 3: PN: EP969015 SEQID: 3 claimedprotein; 622: PN: US20090175821 SEQID: 750 claimed protein; 94: PN: WO0069900SEQID: 750 unclaimed sequence; 95: PN: WO0069900 SEQID: 751 unclaimed sequence;96: PN: WO0069900 SEQID: 752 unclaimed sequence; Bovine b-casomorphin(1-5);Tyr-Pro-Phe-Pro-Gly-OH; b-Casomorphin-5; b-Casomorphin-5 (ox)

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:β-Casomorphin Fragment 1-5 hydrochloride ≥97% (HPLC)
  • Packaging:5mg
  • Price:$ 126
  • Delivery:In stock
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Beta-Casomorphin (1-5) (bovine) acetate salt
  • Packaging:50 mg
  • Price:$ 473
  • Delivery:In stock
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Beta-Casomorphin (1-5) (bovine) acetate salt
  • Packaging:25 mg
  • Price:$ 272
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Beta-Casomorphin (1-5) (bovine) acetate salt
  • Packaging:10 mg
  • Price:$ 136
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Beta-Casomorphin (1-5) (bovine) acetate salt
  • Packaging:250 mg
  • Price:$ 1787.5
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Beta-Casomorphin (1-5) (bovine) acetate salt
  • Packaging:100 mg
  • Price:$ 822
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:TYR-PRO-PHE-PRO-GLY 95.00%
  • Packaging:1MG
  • Price:$ 598.29
  • Delivery:In stock
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:beta-Casomorphin (1-5) bovine
  • Packaging:5mg
  • Price:$ 126
  • Delivery:In stock
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Relevant articles and documentsAll total 9 Articles be found

HOAt.DCHA as co-coupling agent in the synthesis of peptides employing Fmoc-amino acid chlorides as coupling agents: Application to the synthesis of ss-casomorphin

Sureshbabu, Vommina V.,Chennakrishnareddy, Gundala

experimental part, p. 981 - 988 (2009/12/28)

A simple, efficient and racemization free method for the synthesis of peptides employing Fmoc-amino acid chlorides mediated by HOAtDCHA as a co-coupling agent has been described. This protocol is successfully employed in the synthesis of the pentapeptide H-Pro-Gly-VaI-GIy-VaI-OH (PGVGV), and ss-casomorphin (H-Tyr-Pro-Phe-Pro-Gly-OH) in 85 and 80% yields, respectively.

HOBt·DCHA-mediated synthesis of sterically hindered peptides employing Fmoc-amino acid chlorides in both solution-phase and solid phase methods

Sureshbabu, Vommina V.,Sudarshan, Naremaddepalli S.,Chenna Krishna

, p. 2625 - 2637 (2008/12/22)

The synthesis of peptides employing Fmoc-amino acid chlorides in presence of HOBt·DCHA salt in solution as well as by the solid-phase methods is described. The coupling was found to be complete in 30 min and free from racemization. The synthesis of β-casomorphin by solid-phase protocol employing Fmoc-amino acid chloride/HOBt·DCHA in DMF-CH2Cl2 has also been outlined. The final peptide was obtained in 80% yield and was fully characterized. Copyright Taylor & Francis Group, LLC.

A rapid and efficient synthesis of β-casomorphin employing Boc-amino acids and 9-fluorenylmethyl chloroformate as a coupling agent

Babu, V.V. Suresh,Tantry

, p. 2708 - 2712 (2007/10/03)

The synthesis of β-casomorphin H-Tyr-Pro-Phe-Pro-Gly-OH employing Boc group for Nα-protection and 9-fluorenylmethyl chloroformate (Fmoc-Cl) for the formation of peptide bond is described. The protocol employing Fmoc-Cl as coupling reagent is found to be simple, efficient and rapid. All the intermediate peptides as well as the final protected peptide Boc-Tyr( iBu)-Pro-Phe-Pro-Gly-OMe have been isolated and fully characterized. They have been obtained in good yield and with high purity.

Synthesis of β-casomorphin employing Fmoc-amino acid chlorides and t-butyldimethylsilyloxy benzotriazole (TBDMS-OBt)

Tantry, Subramanyam J.,Mathad, Raveendra I.,Suresh Babu, Vommina V.

, p. 2104 - 2108 (2007/10/03)

Coupling of Fmoc-amino acid chlorides can be carried out using t-butyldimethylsilyloxy benzotriazole, the reaction being carried out in organic medium. No addition of base is required. The coupling is fast and racemization free. The workup and isolation of product are easy. Thus, the synthesis of β-casomorphin (Tyr-Pro-Phe-Pro-Gly) is accomplished.

Coupling in the absence of a tertiary base: A method for the deprotonation of hydrochloride salts of peptide esters to free amino peptide esters

Tantry, Subramanyam J.,Ananda,Suresh Babu

, p. 1028 - 1031 (2007/10/03)

The deprotonation of hydrochloride salts of peptide esters is accomplished using activated zinc dust. The reaction is neat and quantitative. Addition of a tertiary base is eliminated during the coupling. The free amino peptide esters have been isolated in good yield and purity. This method is extended for the synthesis of β-casomorphin (Tyr-Pro-Phe-Pro-Gly). During its synthesis, all the intermediate free amino peptide esters have been isolated and characterized.

Process route upstream and downstream products

Process route

Fmoc-Tyr(Bzl)-Pro-Phe-Pro-Gly-OBzl
221174-22-7

Fmoc-Tyr(Bzl)-Pro-Phe-Pro-Gly-OBzl

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
Fmoc-Tyr(Bzl)-Pro-Phe-Pro-Gly-OBzl; With formic acid; palladium on activated charcoal; In methanol; at 20 ℃; for 3h;
With sodium hydrogencarbonate; for 0.333333h;
80%
With formic acid; palladium;
57%
With formic acid; palladium; In methanol;
50%
Z-O-benzyltyrosylprolylphenylalanylprolylglycine benzyl ester
115901-40-1

Z-O-benzyltyrosylprolylphenylalanylprolylglycine benzyl ester

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; In methanol; for 4h;
92%
C<sub>45</sub>H<sub>47</sub>N<sub>5</sub>O<sub>9</sub>
1202377-86-3

C45H47N5O9

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
With diethylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
78%
(S)-N-(fluoren-9-ylmethoxycarbonyl)prolyl chloride
103321-52-4

(S)-N-(fluoren-9-ylmethoxycarbonyl)prolyl chloride

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1.1: 72 percent / TEA; TBDMS-OBt / tetrahydrofuran / 20 °C
2.1: 86 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
3.1: 70 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
4.1: 81 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
5.1: 79 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
6.1: 85 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
7.1: 72 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
8.1: aq. HCOOH / Pd/C / methanol / 3 h / 20 °C
8.2: 80 percent / aq. NaHCO3 / 0.33 h
With formic acid; TEA; di(methyl)tert-butyl(n-butoxy)silane; 4-Aminomethylpiperidine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
Multi-step reaction with 8 steps
1: 75 percent / silver cyanide, triethylamine / toluene / 60 °C / 10-15 min
2: 86 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
3: 64 percent / silver cyanide / toluene / 60 °C / 10-15 min
4: 84 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
5: 79 percent / silver cyanide / toluene / 60 °C / 10-15 min
6: 80 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
7: 72 percent / silver cyanide / toluene / 60 °C / 10-15 min
8: 50 percent / formic acid / palladium black / methanol
With formic acid; silver cyanide; 4-Aminomethylpiperidine; triethylamine; palladium; In methanol; dichloromethane; toluene;
Multi-step reaction with 4 steps
1: 82 percent / KOBt / CH2Cl2
2: 81 percent / 4-(aminomethyl)piperidine / CH2Cl2 / 0.5 h
3: 62 percent / KOBt / CH2Cl2 / Ambient temperature
4: 57 percent / aq. HCOOH / Pd black
With formic acid; 4-Aminomethylpiperidine; 1-Hydroxy-1,2,3-benzotriazole potassium salt; palladium; In dichloromethane;
L-prolylglycine benzyl ester
63496-06-0

L-prolylglycine benzyl ester

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: 70 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
2.1: 81 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
3.1: 79 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
4.1: 85 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
5.1: 72 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
6.1: aq. HCOOH / Pd/C / methanol / 3 h / 20 °C
6.2: 80 percent / aq. NaHCO3 / 0.33 h
With formic acid; di(methyl)tert-butyl(n-butoxy)silane; 4-Aminomethylpiperidine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
Multi-step reaction with 6 steps
1: 64 percent / silver cyanide / toluene / 60 °C / 10-15 min
2: 84 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
3: 79 percent / silver cyanide / toluene / 60 °C / 10-15 min
4: 80 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
5: 72 percent / silver cyanide / toluene / 60 °C / 10-15 min
6: 50 percent / formic acid / palladium black / methanol
With formic acid; silver cyanide; 4-Aminomethylpiperidine; palladium; In methanol; dichloromethane; toluene;
Multi-step reaction with 2 steps
1: 62 percent / KOBt / CH2Cl2 / Ambient temperature
2: 57 percent / aq. HCOOH / Pd black
With formic acid; 1-Hydroxy-1,2,3-benzotriazole potassium salt; palladium; In dichloromethane;
N-(N-fluorenylmethoxycarbonyl-2S-prolyl)-glycine benzyl ester
221174-15-8

N-(N-fluorenylmethoxycarbonyl-2S-prolyl)-glycine benzyl ester

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1.1: 86 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
2.1: 70 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
3.1: 81 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
4.1: 79 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
5.1: 85 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
6.1: 72 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
7.1: aq. HCOOH / Pd/C / methanol / 3 h / 20 °C
7.2: 80 percent / aq. NaHCO3 / 0.33 h
With formic acid; di(methyl)tert-butyl(n-butoxy)silane; 4-Aminomethylpiperidine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
Multi-step reaction with 7 steps
1: 86 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
2: 64 percent / silver cyanide / toluene / 60 °C / 10-15 min
3: 84 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
4: 79 percent / silver cyanide / toluene / 60 °C / 10-15 min
5: 80 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
6: 72 percent / silver cyanide / toluene / 60 °C / 10-15 min
7: 50 percent / formic acid / palladium black / methanol
With formic acid; silver cyanide; 4-Aminomethylpiperidine; palladium; In methanol; dichloromethane; toluene;
Multi-step reaction with 3 steps
1: 81 percent / 4-(aminomethyl)piperidine / CH2Cl2 / 0.5 h
2: 62 percent / KOBt / CH2Cl2 / Ambient temperature
3: 57 percent / aq. HCOOH / Pd black
With formic acid; 4-Aminomethylpiperidine; 1-Hydroxy-1,2,3-benzotriazole potassium salt; palladium; In dichloromethane;
H-Tyr-Pro-Phe-Pro-Gly-OMe
77451-91-3

H-Tyr-Pro-Phe-Pro-Gly-OMe

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
With sodium hydroxide; In methanol; for 3h; pH=8 - 9;
50%
With sodium hydroxide; In methanol; water; for 3h; pH=8 - 9;
50%
H-Phe-Pro-Gly-OBzl
221174-19-2

H-Phe-Pro-Gly-OBzl

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: 79 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
2.1: 85 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
3.1: 72 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
4.1: aq. HCOOH / Pd/C / methanol / 3 h / 20 °C
4.2: 80 percent / aq. NaHCO3 / 0.33 h
With formic acid; di(methyl)tert-butyl(n-butoxy)silane; 4-Aminomethylpiperidine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
Multi-step reaction with 4 steps
1: 79 percent / silver cyanide / toluene / 60 °C / 10-15 min
2: 80 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
3: 72 percent / silver cyanide / toluene / 60 °C / 10-15 min
4: 50 percent / formic acid / palladium black / methanol
With formic acid; silver cyanide; 4-Aminomethylpiperidine; palladium; In methanol; dichloromethane; toluene;
H-Pro-Phe-Pro-Gly-OBzl
221174-21-6

H-Pro-Phe-Pro-Gly-OBzl

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: 72 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
2.1: aq. HCOOH / Pd/C / methanol / 3 h / 20 °C
2.2: 80 percent / aq. NaHCO3 / 0.33 h
With formic acid; di(methyl)tert-butyl(n-butoxy)silane; palladium on activated charcoal; In tetrahydrofuran; methanol;
Multi-step reaction with 2 steps
1: 72 percent / silver cyanide / toluene / 60 °C / 10-15 min
2: 50 percent / formic acid / palladium black / methanol
With formic acid; silver cyanide; palladium; In methanol; toluene;
Fmoc-Phe-Pro-Gly-OBzl
221174-18-1

Fmoc-Phe-Pro-Gly-OBzl

bovine β-casomorphin-5
72122-63-5

bovine β-casomorphin-5

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: 81 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
2.1: 79 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
3.1: 85 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
4.1: 72 percent / TBDMS-OBt / tetrahydrofuran / 0.5 h / 20 °C
5.1: aq. HCOOH / Pd/C / methanol / 3 h / 20 °C
5.2: 80 percent / aq. NaHCO3 / 0.33 h
With formic acid; di(methyl)tert-butyl(n-butoxy)silane; 4-Aminomethylpiperidine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
Multi-step reaction with 5 steps
1: 84 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
2: 79 percent / silver cyanide / toluene / 60 °C / 10-15 min
3: 80 percent / 4-aminomethylpiperidine / CH2Cl2 / 0.5 h
4: 72 percent / silver cyanide / toluene / 60 °C / 10-15 min
5: 50 percent / formic acid / palladium black / methanol
With formic acid; silver cyanide; 4-Aminomethylpiperidine; palladium; In methanol; dichloromethane; toluene;

Global suppliers and manufacturers

Global( 20) Suppliers
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  • Chinapeptides Co,. Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-021-50792271
  • Emails:2880526698@qq.com
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  • Antimex Chemical Limied
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  • Contact Tel:0086-21-50563169
  • Emails:anthony@antimex.com
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  • Finetech Industry Limited
  • Business Type:Trading Company
  • Contact Tel:86-27-87465837
  • Emails:sales@finetechnology-ind.com
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  • Career Henan Chemical Co
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-371-86658258
  • Emails:purchase@coreychem.com
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  • coolpharm Ltd
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  • Emails:salescp@coolpharm.com
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  • Country:China (Mainland)
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