Biotin-PEG4-Acid

Base Information

• Chemical Name: Biotin-PEG4-Acid
• CAS No.: 721431-18-1
• Molecular Formula: C₂₁H₃₇N₃O₈S
• Molecular Weight: 491.606
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID30589237
• Nikkaji Number: J2.716.002F
• Wikidata: Q72482002
• Mol file: 721431-18-1.mol

Synonyms:Biotin-PEG4-Acid;721431-18-1;Biotin-peg4-propionic acid;15-[D-(+)-Biotinylamino]-4,7,10,13-tetraoxapentadecanoic acid;3-Amino(peg4)propionic acid biotinamide;(+)-Biotin-PEG4-CH2CH2COOH;17-oxo-21-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-4,7,10,13-tetraoxa-16-azahenicosanoic acid;(+)-Biotin-PEG24-CH2CH2COOH;MFCD08457831;17-oxo-21-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-4,7,10,13-tetraoxa-16-azahenicosan-1-oic acid;17-Oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,7,10,13-tetraoxa-16-azahenicosan-1-oic acid;15-[D(+)-BIOTINYLAMINO]-4,7,10,13-TETRAOXAPENTADECANOIC ACID;SCHEMBL518031;DTXSID30589237;(+)-Biotin-PEG4-propionic acid;AKOS025404045;s10741;3-[2-[2-[2-[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid;AS-54499;BP-20607;HY-126959;B5562;CS-0108924;W-203624;15-Biotinamino-4,7,10,13-tetraoxa-pentadecanoic acid;15-[D-(+)-Biotinylamino]-4,7,10,13-tetraoxapentadecanoicacid;1-{5-[(3AS,4S,6AR)-2-OXO-HEXAHYDROTHIENO[3,4-D]IMIDAZOL-4-YL]PENTANAMIDO}-3,6,9,12-TETRAOXAPENTADECAN-15-OIC ACID

Chemical Property of Biotin-PEG4-Acid

Chemical Property:

• Boiling Point: 784.8±60.0 °C(Predicted)
• PKA: 4.28±0.10(Predicted)
• PSA: 169.75000
• Density: 1.211±0.06 g/cm3(Predicted)
• LogP: 1.41800
• Storage Temp.: 2-8°C
• Solubility.: Soluble in Water, DMSO, DMF
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 20
• Exact Mass: 491.23013632
• Heavy Atom Count: 33
• Complexity: 598

Purity/Quality:

98%,99%, ^*data from raw suppliers

Biotin-PEG4-CH2CH2COOH 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(S1)CCCCC(=O)NCCOCCOCCOCCOCCC(=O)O)NC(=O)N2
• Isomeric SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCOCCOCCOCCOCCC(=O)O)NC(=O)N2
• Description: Biotin-PEG4-acid is a biotinylation reagent which can react with amine molecules in the presence of activator EDC or HATU. PEG attached to the biotin gives an extended spacer arm that permits the biotin to reach into the binding pocket of the protein. The PEG moiety also increases solubility of Biotin-PEG conjugates considerably.

Technology Process of Biotin-PEG4-Acid

There total 3 articles about Biotin-PEG4-Acid 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:

biotin N-Hydroxysuccinimide ester (35013-72-0) → 1 7-oxo-21-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3 ,4-d]imidazol-4-yl)-4,7,10,13-tetraoxa-16-azahenicosan-1-oic acid (721431-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine

2: trifluoroacetic acid / dichloromethane / 2 h

With triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/acsmedchemlett.1c00625

Reference yield:

tert-butyl 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoate (581065-95-4,872340-65-3) → 1 7-oxo-21-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3 ,4-d]imidazol-4-yl)-4,7,10,13-tetraoxa-16-azahenicosan-1-oic acid (721431-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine

2: trifluoroacetic acid / dichloromethane / 2 h

With triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/acsmedchemlett.1c00625

Reference yield:

C25H45N3O8S → 1 7-oxo-21-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3 ,4-d]imidazol-4-yl)-4,7,10,13-tetraoxa-16-azahenicosan-1-oic acid (721431-18-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h;

DOI:10.1021/acsmedchemlett.1c00625

upstream raw materials:

biotin N-Hydroxysuccinimide ester

tert-butyl 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoate

Downstream raw materials:

N-(3-(1-((R)-2-(4-(1-benzyl-1H-benzo[d]imidazol-2-yl)phenoxy)-1-(piperidin-4-yl)ethyl)-1H-benzo[d]imidazol-2-yl)benzyl)-1-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)-3,6,9,12-tetraoxapentadecan-15-amide trifluoroacetate

Refernces