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(tert-butoxycarbonyl)-L-tyrosyl-L-proline is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 74201-47-1 Structure
  • Basic information

    1. Product Name: (tert-butoxycarbonyl)-L-tyrosyl-L-proline
    2. Synonyms:
    3. CAS NO:74201-47-1
    4. Molecular Formula:
    5. Molecular Weight: 378.425
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 74201-47-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (tert-butoxycarbonyl)-L-tyrosyl-L-proline(CAS DataBase Reference)
    10. NIST Chemistry Reference: (tert-butoxycarbonyl)-L-tyrosyl-L-proline(74201-47-1)
    11. EPA Substance Registry System: (tert-butoxycarbonyl)-L-tyrosyl-L-proline(74201-47-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 74201-47-1(Hazardous Substances Data)

74201-47-1 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 74201-47-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,4,2,0 and 1 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 74201-47:
(7*7)+(6*4)+(5*2)+(4*0)+(3*1)+(2*4)+(1*7)=101
101 % 10 = 1
So 74201-47-1 is a valid CAS Registry Number.

74201-47-1Relevant articles and documents

Short Synthesis of Oxetane and Azetidine 3-Aryl-3-carboxylic Acid Derivatives by Selective Furan Oxidative Cleavage

Bull, James A.,Choi, Chulho,Dubois, Maryne A. J.,Lee Wei Jie, Alvin,Mousseau, James J.,Smith, Milo A.,White, Andrew J. P.

supporting information, p. 5279 - 5283 (2020/08/14)

Four-membered rings remain underexplored motifs despite offering attractive physicochemical properties for medicinal chemistry. Arylacetic acids bearing oxetanes, azetidines, and cyclobutanes are prepared in two steps: a catalytic Friedel-Crafts reaction from four-membered ring alcohol substrates, followed by mild oxidative cleavage. The suitability of the products as building blocks is reflected in their facile purification and amenability to derivatization. Examples include heteroaromatics and aryltriflates, as well as oxetane-derived profen drug analogues and a new endomorphin derivative containing an azetidine amino acid residue.

Endomorphin-1 analogs containing α-methyl-β-Amino acids exhibit potent analgesic activity after peripheral administration

Wang, Yuan,Yang, Junxian,Liu, Xin,Zhao, Long,Yang, Dongxu,Zhou, Jingjing,Wang, Dan,Mou, Lingyun,Wang, Rui

supporting information, p. 4951 - 4955 (2017/07/10)

This study describes the design and synthesis of endomorphin-1 analogs containing C-Terminal aromatic α-methyl-β-Amino acids and an N-Terminal native tyrosine or 2,6-dimethyl-Tyrosine. We show that, in comparison with the parent peptide, these analogs exhibit improved bioactivity and blood-brain barrier penetration after intravenous administration, and have a lower tendency to induce constipation and sedation than morphine.

Design, synthesis, and pharmacological characterization of novel endomorphin-1 analogues as extremely potent μ-opioid agonists

Liu, Xin,Wang, Yuan,Xing, Yanhong,Yu, Jing,Ji, Hong,Kai, Ming,Wang, Zilong,Wang, Dan,Zhang, Yixin,Zhao, Depeng,Wang, Rui

supporting information, p. 3102 - 3114 (2013/06/04)

Recently we reported the synthesis and structure-activity study of endomorphin-1 (EM-1) analogues containing novel, unnatural α-methylene- β-aminopropanoic acids (Map). In the present study, we describe new EM-1 analogues containing Dmt1, (R/S)-βPro2, and (ph)Map4/(2-furyl)Map4. All of the analogues showed a high affinity for the μ-opioid receptor (MOR) and increased stability in mouse brain homogenates. Of the new compounds, Dmt1-(R)-βPro 2-Trp3-(2-furyl)Map4 (analogue 12) displayed the highest affinity toward MOR, in the picomolar range (Ki μ = 3.72 pM). Forskolin-induced cAMP accumulation assays indicated that this analogue displayed an extremely high agonistic potency, in the subpicomolar range (EC50 = 0.0421 pM, Emax = 99.5%). This compound also displayed stronger in vivo antinociceptive activity after iv administration when compared to morphine in the tail-flick test, which indicates that this analogue was able to cross the blood-brain barrier.

A new class of highly potent and selective endomorphin-1 analogues containing α-methylene-β-aminopropanoic acids (map)

Wang, Yuan,Xing, Yanhong,Liu, Xin,Ji, Hong,Kai, Ming,Chen, Zongyao,Yu, Jing,Zhao, Depeng,Ren, Hui,Wang, Rui

experimental part, p. 6224 - 6236 (2012/09/05)

A new class of endomorphin-1 (EM-1) analogues were synthesized by introduction of novel unnatural α-methylene-β-amino acids (Map) at position 3 or/and position 4. Their binding and functional activity, metabolic stability, and antinociceptive activity were determined and compared. Most of these analogues showed high affinities for the μ-opioid receptor and an increased stability in mouse brain homogenates compared with EM-1. Examination of cAMP accumulation and ERK1/2 phosphorylation in HEK293 cells confirmed the agonist properties of these analogues. Among these new analogues, H-Tyr-Pro-Trp-(2-furyl)Map-NH2 (analogue 12) exhibited the highest binding potency (Kiμ = 0.221 nM) and efficacy (EC 50 = 0.0334 nM, Emax = 97.14%). This analogue also displayed enhanced antinociceptive activity in vivo in comparison to EM-1. Molecular modeling approaches were then carried out to demonstrate the interaction pattern of these analogues with the opioid receptors. We found that, compared to EM-1, the incorporation of our synthesized Map at position 4 would bring the analogue to a closer binding mode with the μ-opioid receptor.

Efficient chemo-enzymatic synthesis of endomorphin-1 using organic solvent stable proteases to green the synthesis of the peptide

Sun, Honglin,He, Bingfang,Xu, Jiaxing,Wu, Bin,Ouyang, Pingkai

experimental part, p. 1680 - 1685 (2011/08/07)

Endomorphin-1 (Tyr-Pro-Trp-Phe-NH2, EM-1), an effective analgesic, was efficiently synthesized by a combination of enzymatic and chemical methods. Peptide Boc-Trp-Phe-NH2 was synthesized with a high yield of 97.1% by the solvent-stab

Synthesis, cytotoxic and antimicrobial screening of a proline-rich cyclopolypeptide

Dahiya, Rajiv,Kumar, Akhilesh,Gupta, Rajul

experimental part, p. 214 - 217 (2009/10/02)

Present study describes the first total synthesis of a cyclic heptapeptide, stylisin 1 (8) via coupling of tetrapeptide Boc-L-tyrosinyl-L-prolyl-L-leucyl- L-proline-OH and tripeptide L-phenylalanyl-L-isoleucyl-L-proline- OMe followed by cyclization of lin

Endomorphin-1 analogs with enhanced metabolic stability and systemic analgesic activity: Design, synthesis, and pharmacological characterization

Liu, Hongmei,Zhang, Bangzhi,Liu, Xuefeng,Wang, Changlin,Ni, Jingman,Wang, Rui

, p. 1694 - 1702 (2008/02/03)

We synthesized four new analogs of endomorphin-1 by systematic chemical modifications. To identify the best possible drug candidates for clinical pain management and to investigate the potential contribution of these alterations to the biological activity, their pharmacological properties were determined. All of the analogs showed significantly enhanced metabolic stability. The fact that centrally mediated analgesia following peripheral administration was observed with one of the analogs suggested the approach design undertaken here had validity in the development of endomorphin-1 as a successful opioid drug for the clinic.

Synthetic studies on cyclic octapeptides: Yunnanin F and Hymenistatin

Poojary, Boja,Belagali, Shiddappa L.

, p. 407 - 412 (2007/10/03)

Two biologically active cyclic peptides, Yunnanin F 8 and Hymenistatin 16 were synthesized and the structures were established on the basis of analytical, IR, NMR and mass spectral data. The newly synthesized compounds were screened for their antimicrobia

Structure and conformation of the sodium chloride salt of N-t-Boc-Phenylalanyl-Proline (Boc-Phe-Pro·NaCl) and the dihydrate of N-t-Boc-Tyrosyl-Proline (Boc-Tyr-Pro·2H2O)

Milne,Oliver,Van Rooyen,Roos

, p. 167 - 175 (2007/10/03)

The structure and conformation of the salt of N-t-Boc-Phenylalanyl-Proline (Boc-Phe-Pro-·NaCl) (C19H26N2O5NaCl) (compound 2) and the dihydrate of N-t-Boc-Tyrosyl-Proline (Boc-Tyr-Pro·2H2O) (C19/

Structure and conformation of the monohydrate of N-t-boc-tyrosyl-proline(Boc-Tyr-Pro*H2O)

Oliver, D. W.,Roos, H. M.,Milne, P. J.

, p. 85 - 88 (2007/10/02)

The structure and conformation of the monohydrate of N-t-boc-tyrosyl-proline (Boc-Tyr-Pro*H2O)(C19H26O6N2*H2O) has been investigated with X-ray crystallographic and spectroscopic methods.Boc-Tyr-Pro crystallized in an extended trans conformation in the space group P212121 with cell dimensions a=8.566(1), B=9.996(1), c=24.734(1).The conformation of Boc-Tyr=Pro reflex α-helix type prolines.Three intermolecular hydrogen bonds are observed.Crystal water is involved in two hydrogen bonds (to the hydroxyl group of the C-terminal of the proline residue: to the carbonyl group of the t-Boc functionality) while the hydroxyl group of the tyrosyl residue (to the carbonyl group of the amide bond) is involved in one hydrogen bond.The puckering mode of the pyrrolidine ring of the proline residue is similar to what has been previously observed for other proline-containing peptides.Cis-trans isomerism is observed in the NMR spectra of Boc-Tyr-Pro with a predominance for the extended side chain for the tyrosyl residue. KEY WORDS: Dipeptides, proline, NMR,hydrogen bonds.

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