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Quality Control of Biotin-PFP ester Purity: 95% SDS Specification

COA

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NMR

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Product Citations

Primary Amine-Functionalized Ligand Substitution and Biotinylation of Co (III) for Ligand-Anchored Artificial Metalloenzymes

Adams, Milo A ; Kincade, Jack A ; Runyan, Elle C ; Torraco, Ashley N ;

Abstract: Group IX metals in the+ 3-oxidation state can be incorporated into [Cp* MCl2] 2 complexes for the design and synthesis of new artificial metalloenzymes for biological functions. While previous studies have applied the more costly and less abundant rhodium-or iridium-(III) metals, use of a cobalt (III) metal center provides a low-cost route to preparing artificial metalloenzymes. Herein, a new metal cofactor is acquired through synthesis of a primary amine-functionalized Cp* ligand and subsequent complexation with a Co (III) metal center. Key signals corresponding to the Cp* and NH2 groups are visible by Fourier Transform Infrared spectroscopy where the aromatic signal of the Cp* and the stretching mode of the primary amine are present in their characteristic regions, supporting the formation of a tentatively assigned bis [dichloro-ⴄ5 (1-ethylamine-2, 3, 4, 5-tetramethylcylopentadienyl)-cobalt (III)]. Biotinylation of this complex would allow for pairing with engineered proteins to foster catalytic C—H activation, improving enzymatic processes in biological and biochemical applications.

Purchased from AmBeed: 120550-35-8

Product Details of Biotin-PFP ester

CAS No. :	120550-35-8
Formula :	C₁₆H₁₅F₅N₂O₃S
M.W :	410.36
SMILES Code :	[H][C@]12CS[C@@H](CCCCC(=O)OC3=C(F)C(F)=C(F)C(F)=C3F)[C@@]1([H])NC(=O)N2
MDL No. :	MFCD09952636
InChI Key :	DKTMDBQDSYQUEV-LEJLMFORSA-N
Pubchem ID :	11122445

Safety of Biotin-PFP ester

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Biotin-PFP ester

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 120550-35-8 ]

[ 120550-35-8 ] Synthesis Path-Downstream 1~35

1
[ 120550-35-8 ]
[ 79750-47-3 ]
(S)-3-(4-Benzyloxycarbonylamino-phenyl)-2-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-propionic acid methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 1401 - 1404.

2
[ 14533-84-7 ]
[ 58-85-5 ]
[ 120550-35-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine; In N,N-dimethyl-formamide; at 0 - 70℃; for 1h;	D-Biotin (1.00 g, 4.09 mmol) was dissolved in 20 mL DMF at 70 C and allowed to cool to rt. TEA (0.83g, 1.14 mL, 8.19 mmol) was added, followed by pentafluorophenyl trifluoroacetate (1.60 g, 0.98 mL, 5.73 mmol). The reaction was allowed to stir for 1 h at 0 C and became pink. Solvent was reduced to 1 mL in vacuo and the crude material was triturated with cold diethyl ether. The pFp ester product was recovered as a white solid (1.54 g, 96%). Biotin-pFp ester (1.00 g, 2.44 mmol) was dissolved in 10 mL DMF and cooled to 0 C. A flask containing a suspension of NaBH4 (3.4 mmol) in dry DMF (5 mL) was also cooled to 0 C. The pFp-ester was transferred dropwise via a cannula over 15 min and the mixture was stirred at 0 C. The reaction was followed by TLC and upon completion the cold mixture was acidified with 1 N HC1 and reduced to 1 mL in vacuo. The residue was triturated with cold diethyl ether and the product alcohol was recovered as a white solid (0.528 g, 94%). The alcohol (0.528 g, 2.29 mmol) and TEA (0.39 ml, 1.2 eq) were dissolved in DMF (10 mL) and added dropwise to a stirred solution of 4-nitrophenyl chloroformate (4-NCF, 1.38 g, 6.87 mmol, 3.0 eq) in DMF (10 mL) over a period of 1 h at -10C. The reaction mixture was allowed to warm to rt, stirred overnight, and subsequently and reduced to 1 mL in vacuo. The residue was triturated with cold diethyl ether. The nitrophenol carbonate product was recovered as a white solid (0.96 g, 95%). Fmoc-L-Lys-OH (1.03 g, 2.83 mmol, 1.3 eq.) was suspended under argon in anhydrous DMF (10 ml) containing DiPEA (0.50 ml, 1.3 eq.). To this white suspension, a clear solution of the nitrophenol-carbonate (2.18 mmol, 1.0 eq.) in anhydrous DMF (10 mL) was added drop wise under argon at rt over a period of 2 h. The reaction mixture was stirred for additional 4 h at rt, before the solution as acidified to pH 2 with 1 N HC1. All volatiles were evaporated under reduced pressure and the residue was triturated with cold diethyl ether. The crude product was purified by column chromatography (DCM : MeOH 95 : 5 v/v) to give the Fmoc-protected ncAA as a white solid. The Fmoc- protected ncAA was dissolved in 20% piperidine in DMF (5 ml) and stirred for 1 h at r.t.. All volatiles were removed under reduced pressure and the residue was triturated with cold diethyl ether. Drying of the residue in vaccuum yield the pure ncAA as a white powder (0.622 g, 71 %). 1H-NMR (D6-DMSO, 400 MHz): delta = 1.30-1.45 (m, 6H), 1.50-1.65 (m, 4H), 1.85 (m, 2H), 2.65 (d, J = 12.2 Hz, 1H), 2.84 (dd, J= 5.0 Hz, J= 12.2 Hz, 1H), 2.95 (m, 2H), 3.13 (m, 1H), 3.42 (m, 1H), 3.66 (m, 1H), 3.85 (dd, J= 13.8 Hz, J = 1.0 Hz 1H), 3.93 (t, J= 7.5 Hz, 2H), 4.17 (dd, J= 8.2 Hz, J= 7.3 Hz, 1H), 4.35 (dd, J= 8.1 Hz, J= 7.2 Hz, 1H), 7.11 (t, J= 5.4 Hz, 1H), 8.50 (br, 3H), 8.53 (br, 1H), 8.68 (br, 1H).13C-NMR (D6-DMSO, 100 MHz): 13C-NMR (CDCI3, 100 MHz): delta = 171.44, 163.29, 156.82, 64.00, 61.61, 60.35, 59.79, 55.95, 52.28, 39.10, 30.05, 29.35, 29.02, 28.78, 28,73, 25.91, 22.05. HR-MS (C17H31N4O5S): calculated: 403.20097, found: 403.20159.
81%		Biotin (5 g; 23.1 mmol; 1.0 eq) is suspended in anhydrous DMF (50 ml) and pyridine (2.07 ml; 25.4 mmol; 1.1 eq). After stirring for 5 minutes, pentafluorophenyl trifluoroacetate (PFP-TFA: 4.621 ml, i.e. 7.50 g; 25.4 mmol; 1.1 eq) is added. After stirring for one night, the reaction is finished, and the solvents are evaporated on the rotary evaporator. The evaporation residue is taken up in 100 ml of ethyl ether to suspend it, then filtered off on a fritted filter, and the cake is rinsed with a minimum of ether. Note: in the TLC a small trace of biotin is observed, but that will have no impact on what follows. m=7.106 g. Yield: 81%. TLC eluent: DCM/MeOH: 90/10.

References: [1]Patent: WO2018/207077,2018,A1 .Location in patent: Paragraph 0082.
[2]Organic Letters,2013,vol. 15,p. 1406 - 1409.
[3]Patent: US9266902,2016,B2 .Location in patent: Page/Page column 21.
[4]Chemistry of Natural Compounds,1989,vol. 25,p. 350 - 353.
Khimiya Prirodnykh Soedinenii,1989,p. 404 - 408.
[5]Journal of Medicinal Chemistry,2019,vol. 62,p. 5522 - 5540.
[6]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 625 - 637.
[7]Journal of the American Chemical Society,2009,vol. 131,p. 12091 - 12093.

3
[ 59483-84-0 ]
[ 58-85-5 ]
[ 120550-35-8 ]

References: [1]Chemistry of Natural Compounds,1989,vol. 25,p. 350 - 353.
Khimiya Prirodnykh Soedinenii,1989,p. 404 - 408.

4
[ 120550-35-8 ]
[ 60-32-2 ]
D-biotinyl-ε-aminocaproic acid [ No CAS ]

References: [1]Chemistry of Natural Compounds,1989,vol. 25,p. 350 - 353.
Khimiya Prirodnykh Soedinenii,1989,p. 404 - 408.

5
[ 120550-35-8 ]
[ 167700-41-6 ]
biotinyl-3-amino-O¹-dimethoxytrityl-1,2-propanediol [ No CAS ]

References: [1]Russian Journal of Bioorganic Chemistry,1994,vol. 20,p. 520 - 528.
Bioorganicheskaya Khimiya,1994,vol. 20,p. 955 - 966.

6
[ 771-61-9 ]
[ 58-85-5 ]
[ 120550-35-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	Biotin (2.95 g, 12.00 mmol) was dissolved in DMF (10 mL), and Pfp-OH (2.80 g, 15.20 mmol) was added to the biotin solution before EDC.HCl (5.70 g, 29.70 mmol) in DMF (15 mL) were added to the mixture at 0 C over 30 min. The mixture stirred overnight at room temperature under nitrogen atmosphere. The product washed with DCM. White powder was obtained with a yield of 90% (4.50 g). The product was used in the next step without further purification. 1H NMR (D2O): d 1.41-1.69 (m, 6H, CH2), 2.57 (d, 1H,CH2), 2.77-2.85 (m, 3H, CH2), 3.11-3.12 (m, 1H, CH), 4.14 (t, 1H, CH), 4.30 (t, 1H, CH), 6.37 (d, 2H, NH).
	With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃;	EXAMPLE lO[D-(+)-biotinyl]-L-aspartate alpha-benzyl ester (14)To a suspension of D-Biotin (2.0 g, 8.19 mmol) in DMF (52 mL) was added pentafluorophenol (1.6 g, 15.6 mmol) followed by DCC (2.5 g, 12.3 mmol). The reaction mixture was allowed to stir, under nitrogen atmosphere, overnight at RT. The reaction mixture remained a suspension and was filtered off and concentrated. The residue was taken up into Et2theta and stirred for several minutes after which the suspension was filtered an dried und vacuum to give a white solid (2.58 g) ESI-MS: 411 [M+H]+. The solid was dissolved in DMF (90 mL) and Et3N (1.24 mL, 8.82 mmol, 1.4 equiv.) was added. H-Asp-OBn was added in portions as a solid. After approximately 15 min the reaction mixture became clear and an additional 2h stirring was allowed. The reaction mixture was concentrated under reduced pressure and water was added followed by MeOH (3:1). The solid formed was filtered off, washed with Et2theta and dried under vacuum to give compound 14 as a white solid (2.92 g, 77 %) ESI-MS: 450 [M+H]+.

References: [1]Synthetic Communications,1996,vol. 26,p. 2531 - 2547.
[2]Journal of the American Chemical Society,2009,vol. 131,p. 7954 - 7955.
[3]Russian Journal of Bioorganic Chemistry,1994,vol. 20,p. 520 - 528.
Bioorganicheskaya Khimiya,1994,vol. 20,p. 955 - 966.
[4]Organic and biomolecular chemistry,2003,vol. 1,p. 950 - 959.
[5]Chinese Chemical Letters,2017,vol. 28,p. 832 - 838.
[6]Biomacromolecules,2012,vol. 13,p. 2831 - 2842.
[7]Organic Letters,2008,vol. 10,p. 4453 - 4455.
[8]Russian Journal of Bioorganic Chemistry,2017,vol. 43,p. 386 - 396.
Bioorg. Khim.,2017,vol. 43,p. 377 - 387,11.
[9]Patent: WO2007/42469,2007,A2 .Location in patent: Page/Page column 20.

7
[ 120550-35-8 ]
[ 148704-81-8 ]
[ 148704-82-9 ]

References: [1]Synthetic Communications,1996,vol. 26,p. 2531 - 2547.

8
[ 120550-35-8 ]
[ 1926-80-3 ]
methyl 6-(+)-biotinylamidohexanoate [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2000,vol. 43,p. 309 - 322.

9
[ 120550-35-8 ]
2-{2-[6-amino-2-(2-tert-butoxycarbonylamino-5-guanidino-pentanoylamino)-hexanoylamino]-3-tert-butoxycarbonyl-propionylamino}-3-methyl-butyric acid tert-butyl ester [ No CAS ]
Boc-Arg(HCl)-Lys[(+)-biotinyl]-Asp(Ot-Bu)-Val-Ot-Bu [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2000,vol. 43,p. 309 - 322.

10
[ 120550-35-8 ]
H-Arg(HCl)-Lys(Boc)-Asp(Ot-Bu)-Val-Ot-Bu*HCl [ No CAS ]
[(+)-biotinyl]-Arg(HCl)-Lys(Boc)-Asp(Ot-Bu)-Val-Ot-Bu [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2000,vol. 43,p. 309 - 322.

11
[ 120550-35-8 ]
[ 101187-40-0 ]
[ 418759-44-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 625 - 637.

12
[ 929-59-9 ]
[ 120550-35-8 ]
[ 138529-46-1 ]

References: [1]Organic and biomolecular chemistry,2003,vol. 1,p. 950 - 959.
[2]Biomacromolecules,2012,vol. 13,p. 2831 - 2842.

13
[ 120550-35-8 ]
(3aR,8bS)-7-Amino-3-[1-((R)-4-methyl-5-oxo-2,5-dihydro-furan-2-yloxy)-meth-(E)-ylidene]-3,3a,4,8b-tetrahydro-indeno[1,2-b]furan-2-one [ No CAS ]
N₁-[(3aRS,8bSR)-3-((E)-1-[(2RS)-4-methyl-5-oxo-2,5-dihydro-2-furanyl]oxymethylidene)-2-oxo-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-7-yl]-5-(2-oxoperhydrothieno[3,4-d]imidazol-4-yl)pentanamide [ No CAS ]

References: [1]Organic and biomolecular chemistry,2003,vol. 1,p. 950 - 959.

14
[ 120550-35-8 ]
[ 486445-72-1 ]
5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid (3-{2-[2-(3-{(R)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-hydroxy-butyrylamino}-propoxy)-ethoxy]-ethoxy}-propyl)-amide [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 4607 - 4610.

15
[ 120550-35-8 ]
N-(3-amino-propyl)-N-[4-(4-azidomethyl-benzoyl)-benzyl]-4-nitro-benzenesulfonamide [ No CAS ]
5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid {3-[[4-(4-azidomethyl-benzoyl)-benzyl]-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide [ No CAS ]

References: [1]Chemical Communications,2003,p. 2244 - 2245.

16
[ 120550-35-8 ]
N-(3-amino-propyl)-N-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-benzoyl]-benzyl}-4-nitro-benzenesulfonamide [ No CAS ]
5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid {3-[{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-benzoyl]-benzyl}-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide [ No CAS ]

References: [1]Chemical Communications,2003,p. 2244 - 2245.

17
[ 120550-35-8 ]
N-(8-amino-octyl)-N-[4-(4-azidomethyl-benzoyl)-benzyl]-4-nitro-benzenesulfonamide [ No CAS ]
5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid {8-[[4-(4-azidomethyl-benzoyl)-benzyl]-(4-nitro-benzenesulfonyl)-amino]-octyl}-amide [ No CAS ]

References: [1]Chemical Communications,2003,p. 2244 - 2245.

18
[ 77837-46-8 ]
[ 120550-35-8 ]
N,N-dimethyl-N'-(4-biotinamidophenylsulfonyl)-ethylenediamine [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 8320 - 8328.

19
C₃₇H₃₈N₂OP₂ [ No CAS ]
[ 120550-35-8 ]
N-((R)-1-(bis(2-(diphenylphosphino)ethyl)amino)-1-oxo-3-phenylpropan-2-yl)-5-((3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide [ No CAS ]

References: [1]Chemical Communications,2005,p. 4815 - 4817.

20
C₃₇H₃₈N₂OP₂ [ No CAS ]
[ 120550-35-8 ]
N-((S)-1-(bis(2-(diphenylphosphino)ethyl)amino)-1-oxo-3-phenylpropan-2-yl)-5-((3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide [ No CAS ]

References: [1]Chemical Communications,2005,p. 4815 - 4817.

21
C₃₃H₃₆N₂OP₂ [ No CAS ]
[ 120550-35-8 ]
(R)-N,N-bis(2-(diphenylphosphino)ethyl)-1-(5-((3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl)pyrrolidine-2-carboxamide [ No CAS ]

References: [1]Chemical Communications,2005,p. 4815 - 4817.

22
C₃₃H₃₆N₂OP₂ [ No CAS ]
[ 120550-35-8 ]
(S)-N,N-bis(2-(diphenylphosphino)ethyl)-1-(5-((3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl)pyrrolidine-2-carboxamide [ No CAS ]

References: [1]Chemical Communications,2005,p. 4815 - 4817.

23
C₃₁H₄₃F₃N₈O₅S [ No CAS ]
[ 120550-35-8 ]
[ 943601-18-1 ]