TUFTSIN

Base Information

• Chemical Name: TUFTSIN
• CAS No.: 9063-57-4
• Molecular Formula: C21H40 N8 O6
• Molecular Weight: 500.599
• Mol file: 9063-57-4.mol

Synonyms:L-Arginine,N2-[1-(N2-L-threonyl-L-lysyl)-L-prolyl]-; 100: PN: US20060127404 SEQID: 100claimed sequence; 11: PN: WO2004002417 SEQID: 100 claimed protein; 1271: PN:US20090175821 SEQID: 1558 claimed protein; 137: PN: US20030119021 SEQID: 137unclaimed protein; 14: PN: US20030226155 SEQID: 14 unclaimed protein; 14: PN:WO2007076032 TABLE: 59 unclaimed sequence; 1: PN: US20040132667 SEQID: 1unclaimed protein; 229: PN: WO0024782 SEQID: 263 claimed protein; 253: PN:WO0069900 SEQID: 1558 unclaimed protein; 258: PN: WO0069900 SEQID: 1563unclaimed protein; 27: PN: WO2009126037 PAGE: 5 unclaimed sequence; 29: PN:US6720141 SEQID: 26 unclaimed protein; 2: PN: WO2009033726 PAGE: 99 claimedprotein; 30: PN: WO2006010057 SEQID: 60 unclaimed protein; 32: PN: WO2009105671SEQID: 32 unclaimed protein; 50: PN: WO03084477 PAGE: 24 claimed protein; 52:PN: US20070031440 SEQID: 14 unclaimed sequence; 52: PN: WO2007047969 SEQID: 52unclaimed sequence; 56: PN: WO0183525 TABLE: 4 claimed protein; 60: PN:US20090258017 SEQID: 60 claimed protein; 60: PN: WO2007124090 SEQID: 60 claimedsequence; 67: PN: WO2004002424 SEQID: 100 claimed protein; 7: PN: WO02055543SEQID: 12 unclaimed protein; L-Threonyl-L-lysyl-L-prolyl-L-arginine; Tafcine;Taftsin; Taphcin; Tuftsin

Chemical Property of TUFTSIN

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 3.60±0.21(Predicted)
• Flash Point: °C
• PSA: 249.98000
• Density: 1.48g/cm³
• LogP: 0.44320
• Storage Temp.: −20°C

Purity/Quality:

99%, ^*data from raw suppliers

Tuftsin 98.40% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TUFTSIN

There total 16 articles about TUFTSIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

Benzyloxycarbonylthreonyl(ε-tert-butoxycarbonyllysyl)prolylarginine (78432-02-7) → thr-Lys-Pro-Arg (9063-57-4,112592-90-2)

Guidance literature:

With hydrogen bromide; In trifluoroacetic acid; for 0.333333h;

DOI:10.1007/BF00765712

Reference yield: 59.0%

Boc-Thr(OBn)-Lys(2Cl,Z)-Pro-Arg(Tos)-OBn (154509-00-9) → thr-Lys-Pro-Arg (9063-57-4,112592-90-2)

Guidance literature:

With Ethyl methyl sulfide; methyl-phenyl-thioether; methoxybenzene; In trifluoroacetic acid; for 1h;

DOI:10.1016/S0040-4020(01)81544-1

Reference yield:

H-Arg(Tos)-OBzl (29388-63-4) → thr-Lys-Pro-Arg (9063-57-4,112592-90-2)

Guidance literature:

Multi-step reaction with 6 steps

1: DCC / HOBt / dimethylformamide / 0 °C

2: 2.) NaHCO₃ / 1.) TFA, room temp., 1.5 hrs; 2.) water, dichloromethane, room temp, 0.5 hr

3: DCC / HOBt / dimethylformamide / 0 °C

4: 2.) NaHCO₃ / 1.) TFA, room temp., 1.5 hrs; 2.) water, dichloromethane, room temp, 0.5 hr

5: DCC / HOBt / dimethylformamide / 0 °C

6: 59 percent / anisole, ethyl methyl sulfide, thioanisole / trifluoroacetic acid / 1 h

With Ethyl methyl sulfide; methyl-phenyl-thioether; sodium hydrogencarbonate; methoxybenzene; dicyclohexyl-carbodiimide; benzotriazol-1-ol; In N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1016/S0040-4020(01)81544-1

upstream raw materials:

Benzyloxycarbonylthreonyl(ε-tert-butoxycarbonyllysyl)prolylarginine

Boc-Thr(OBn)-Lys(2Cl,Z)-Pro-Arg(Tos)-OBn

H-Arg(Tos)-OBzl

Boc-Arg(Tos)-OH

Downstream raw materials:

L-threonine

L-lysine

L-arginine

L-proline

Refernces

N-GLYCOSIDES. V. 3-GLYCOSYL-4-HYDROXYHEXAHYDROPYRIMIDINE-2-THIONES AND THEIR ACYCLIC GLYCOSYLTHIOUREA PRECURSORS AS STIMULATORS OF NON-SPECIFIC RESISTANCE TO INFECTION

10.1007/BF01148382

The research focused on investigating the immuno-stimulating properties of certain glycosylthiourea and 3-glycosyl-4-hydroxyhexahydropyrimidine-2-thiones as stimulators of non-specific resistance to infection. The purpose was to understand the action of these compounds on natural immunity, particularly on the resistance of an organism to infection. The study utilized a series of compounds, including 3[B-D-gluco(galacto)-pyranosyl]-4-hydroxyhexahydropyrimidine-2-thiones (I and II), N'-[B-D-gluco(galacto)pyranosyl]-N3-(2-methyl-4-oxopentyl-2)thiourea (III and IV), and N'-[B-D-gluco(galacto)-pyranosyl]-NS-(3,3-diethoxypropyl)thiourea (V and VI), along with their aglycones. The synthesis involved chemicals such as 2,3,5-tri-O-acetyl-8-D-ribofuranosylisothiocyanate (VIII), 4-amino-4-methyl-2-pentanone (IX), and 3,3-diethoxypropylamine (X). The conclusions drawn from the biological experiments indicated that all test compounds demonstrated some level of stimulating action, with an index of resistance ranging from 2 to 6, and were comparable to known immunostimulators like taftsin, rigin, and levamisole. The effectiveness of these compounds was associated with an increase in proliferating processes in lymphoid and hematopoietic tissues, as evidenced by an increase in the number of stem cells in the spleens of lethally irradiated mice that received the test compounds.

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