Biotin-PEG2-Amine

Base Information

• Chemical Name: Biotin-PEG2-Amine
• CAS No.: 138529-46-1
• Molecular Formula: C16H30N4O4S
• Molecular Weight: 374.505
• Hs Code.: 2918999090
• UNII: B5M6KM3UCN
• DSSTox Substance ID: DTXSID301030316
• Nikkaji Number: J1.347.563F
• Wikipedia: Biotin PEG2 amine
• Wikidata: Q4915359
• ChEMBL ID: CHEMBL4216868
• Mol file: 138529-46-1.mol

Synonyms:138529-46-1;Biotin-PEG2-Amine;Biotin-DADOO;Biotin-PEG2-NH2;(+)-Biotin-(PEO)3-amine;BIOTIN PEG2 AMINE;aminobiotin;N-[2-[2-(2-Aminoethoxy)ethoxy]ethyl] biotinamide;biotinyl-3,6-dioxaoctanediamine;(+)-Biotin-PEG2-CH2CH2NH2;B5M6KM3UCN;N-BIOTINYL-3,6-DIOXAOCTANE-1,8-DIAMINE;(+)-biotinyl-3,6-dioxaoctanediamine;N-(2-(2-(2-Aminoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide;(3aS,4S,6aR)-N-(2-(2-(2-Aminoethoxy)ethoxy)ethyl)hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-pentanamide;5-((3aS,4S,6aR)-2-Oxo-hexahydro-1H-thieno(3,4-d)imidazol-4-yl)-N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)pentanamide;N-Biotinyl-3,6-dioxaoctanediamine;MFCD09264745;5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]-N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}pentanamide;UNII-B5M6KM3UCN;EZ-Link Amine-PEO2-Biotin;(+)-Biotin-PEG2-ethylamine;SCHEMBL3179829;CHEMBL4216868;LWISPDYGRSGXME-YDHLFZDLSA-N;DTXSID301030316;BCP24879;HY-D0980;AS-74919;BP-20671;n-(8-amino-3,6-dioxaoctanyl)biotinamide;n-(8-amino-3,6-dioxaoctanyl) biotinamide;N-biotinoyl-1,8-diamino-3,6-dioxaoctane;CS-0028293;H11488;A926629;A1-06587;J-007153;Q4915359;EZ-Link Amine-PEO2-BiotinBiotinyl-3,6-dioxaoctanediamine;1H-THIENO(3,4-D)IMIDAZOLE-4-PENTANAMIDE, N-(2-(2-(2-AMINOETHOXY)ETHOXY)ETHYL)HEXAHYDRO-2-OXO-, (3AS-(3A.ALPHA.,4.BETA.,6A.ALPHA.))-;1H-Thieno(3,4-d)imidazole-4-pentanamide, N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)hexahydro-2-oxo-, (3as-(3aalpha,4beta,6aalpha))-;1H-Thieno[3,4-d]imidazole-4-pentanamide, N-[2-[2-(2-aminoethoxy)ethoxy]ethyl]hexahydro-2-oxo-, (3aS,4S,6aR)-;5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[2-(2-aminoethoxy)ethoxy]ethyl]pentanamide

Chemical Property of Biotin-PEG2-Amine

Chemical Property:

• Melting Point: 109-110℃
• Boiling Point: 689.4±55.0 °C(Predicted)
• PKA: 13.90±0.40(Predicted)
• PSA: 140.01000
• Density: 1.172±0.06 g/cm3(Predicted)
• LogP: 1.56910
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Soluble in Water, DMSO, DMF
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 374.19877662
• Heavy Atom Count: 25
• Complexity: 427

Purity/Quality:

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

Biotin-PEG2-Amine >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(S1)CCCCC(=O)NCCOCCOCCN)NC(=O)N2
• Isomeric SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCOCCOCCN)NC(=O)N2
• Description: Biotin-PEG2-amine is a biotinylation that can react with NHS ester or carboxylic acid in the presence of EDC or HATU.

Technology Process of Biotin-PEG2-Amine

There total 12 articles about Biotin-PEG2-Amine 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: 100.0%

tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate (175885-18-4) → N-(8-amino-3,6-dioxaoctanyl)biotinamide (138529-46-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 6h;

DOI:10.1039/c7cc03252h

Reference yield: 95.0%

3,6-dioxa-1,8-diaminooctane (929-59-9,892154-56-2) + biotin (58-85-5,22879-79-4) → N-(8-amino-3,6-dioxaoctanyl)biotinamide (138529-46-1)

Guidance literature:

biotin; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 60 ℃; for 3h;

3,6-dioxa-1,8-diaminooctane; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jacs.0c05605

Reference yield: 87.0%

3,6-dioxa-1,8-diaminooctane (929-59-9,892154-56-2) + biotin pentafluorophenyl ester (120550-35-8) → N-(8-amino-3,6-dioxaoctanyl)biotinamide (138529-46-1)

Guidance literature:

With triethylamine; at 20 ℃; for 0.5h;

DOI:10.1039/b210678g

upstream raw materials:

tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate

N-butylamine

3,6-dioxa-1,8-diaminooctane

biotin pentafluorophenyl ester

Downstream raw materials:

N₅-[2-(N₃-{2-[2-(2-biotinylaminoethoxy)ethoxy]ethyl}-N₂-fluorenylmethyloxycarbonylguanidino)ethylcarbonyl]-N₁-(tritylaminooxyacetyl)-1,5-diaminonaphthalene

1-(N₃-{2-[2-(2-biotinylaminoethoxy)ethoxy]ethyl}-N₂-fluorenylmethyloxycarbonylguanidino)-N₅-(tritylaminooxyacetyl)-5-aminonaphthalene

Refernces

• 1、 Mühlberg, Michaela,Hoesl, Michael G.,Kuehne, Christian,Dernedde, Jens,Budisa, Nediljko,Hackenberger, Christian P. R.. "Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds". . p. 784 - 791. Retrieved 2015.
• 2、 Fung, Yi Man Eva,Huang, Yiran,Li, Xiaoyu,Peng, Jianzhao,Song, Yinan,Xiong, Feng. "Introducing aldehyde functionality to proteins using ligand-directed affinity labeling". . p. 6134 - 6137. Retrieved 2020.
• 3、 Pinkin, Nicholas K.,Power, Amanie N.,Waters, Marcey L.. "Late stage modification of receptors identified from dynamic combinatorial libraries". . p. 10939 - 10945. Retrieved 2015.
• 4、 Uvyn, Annemiek,De Coen, Ruben,De Wever, Olivier,Deswarte, Kim,Lambrecht, Bart N.,De Geest, Bruno G.. "Cell surface clicking of antibody-recruiting polymers to metabolically azide-labeled cancer cells". . p. 10952 - 10955. Retrieved 2019.
• 5、 Braun, Martin,Camps,Vostrowsky, Otto,Hirsch, Andreas,Endress, Emil,Bayerl, Thomas M.,Birkert, Oliver,Gauglitz, Guenter. "Synthesis of a biotinated lipofullerene as a new type of transmembrane anchor". . p. 1173 - 1181. Retrieved 2000.
• 6、 Uvyn, Annemiek,De Coen, Ruben,Gruijs, Mandy,Tuk, Cees W.,De Vrieze, Jana,van Egmond, Marjolein,De Geest, Bruno G.. "Efficient Innate Immune Killing of Cancer Cells Triggered by Cell-Surface Anchoring of Multivalent Antibody-Recruiting Polymers". . p. 12988 - 12993. Retrieved 2019.
• 7、 Lyu, Zhigang,Zhao, Yue,Buuh, Zakey Yusuf,Gorman, Nicole,Goldman, Aaron R.,Islam, Md Shafiqul,Tang, Hsin-Yao,Wang, Rongsheng E.. "Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine-Thiol Displacement Reaction". supporting information. p. 1341 - 1347. Retrieved 2021/02/01.