Home Cart 0 Sign in  

[ CAS No. 138529-46-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 138529-46-1
Chemical Structure| 138529-46-1
Structure of 138529-46-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 138529-46-1 ]

Related Doc. of [ 138529-46-1 ]

Alternatived Products of [ 138529-46-1 ]

Product Details of [ 138529-46-1 ]

CAS No. :138529-46-1 MDL No. :MFCD09264745
Formula : C16H30N4O4S Boiling Point : -
Linear Structure Formula :- InChI Key :LWISPDYGRSGXME-YDHLFZDLSA-N
M.W : 374.50 Pubchem ID :11199678
Synonyms :
EZ-Link Amine-PEO2-Biotin;Biotinyl-3,6-dioxaoctanediamine;Biotin-PEG2-amine

Safety of [ 138529-46-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 138529-46-1 ]

* 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 [ 138529-46-1 ]

[ 138529-46-1 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 872093-86-2 ]
  • [ 108-30-5 ]
  • [ 84624-27-1 ]
  • [ 75932-02-4 ]
  • [ 138529-46-1 ]
  • N-[4-(3-(13-amino-4,7,10-trioxa-tridecylcarbamoyl)-propionylsulfamoyl)-butyryl]-[polystyrene-poly(ethylene glycol) amine resin] [ No CAS ]
  • 2-aminoethyl α-D-mannopyranoside [ No CAS ]
  • C95H152N14O38S [ No CAS ]
  • 3
  • [ 872093-86-2 ]
  • [ 108-30-5 ]
  • [ 84624-27-1 ]
  • [ 75932-02-4 ]
  • [ 138529-46-1 ]
  • N-[4-(3-(13-amino-4,7,10-trioxa-tridecylcarbamoyl)-propionylsulfamoyl)-butyryl]-[polystyrene-poly(ethylene glycol) amine resin] [ No CAS ]
  • 2-aminoethyl α-L-fucopyranoside [ No CAS ]
  • C95H152N14O35S [ No CAS ]
  • 4
  • [ 881212-56-2 ]
  • [ 138529-46-1 ]
  • [ 881212-59-5 ]
  • 5
  • [ 29270-56-2 ]
  • [ 138529-46-1 ]
  • C22H31N7O7S [ No CAS ]
  • 6
  • [ 411220-47-8 ]
  • [ 138529-46-1 ]
  • C16(13)C4H34N4O7S [ No CAS ]
  • 10
  • [ 138529-46-1 ]
  • [ 505076-96-0 ]
  • 11
  • [ 138529-46-1 ]
  • [ 505077-06-5 ]
  • 12
  • [ 138529-46-1 ]
  • N-[(S)-2-(4-Benzoyl-benzoylamino)-1-([2-(2-{2-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethylcarbamoyl]-methyl}-carbamoyl)-ethyl]-succinamic acid 2,5-dioxo-3-sulfo-pyrrolidin-1-yl ester [ No CAS ]
  • 13
  • [ 138529-46-1 ]
  • C43H50(2)H4N8O16S2 [ No CAS ]
  • 14
  • [ 138529-46-1 ]
  • [ 505077-01-0 ]
  • 15
  • [ 138529-46-1 ]
  • C39H55N9O24S3 [ No CAS ]
  • 16
  • [ 138529-46-1 ]
  • C51H79N11O27S3 [ No CAS ]
  • 17
  • [ 138529-46-1 ]
  • 2-{2-[2-(2-biotinamidoethoxy)-ethoxy]ethylamino}ethyl 2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-α-D-galactopyranosiduronamide [ No CAS ]
  • 18
  • [ 138529-46-1 ]
  • 4-Isothiocyanato-benzoic acid (R)-2-[2-methoxy-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzyloxycarbonylamino]-1-[2-(2-{2-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethylcarbamoyl]-ethyl ester [ No CAS ]
  • 19
  • [ 101187-31-9 ]
  • [ 138529-46-1 ]
  • 20
  • [ 58-85-5 ]
  • streptavidin-fluorescein isothiocyanate [ No CAS ]
  • [ 138529-46-1 ]
  • 21
  • 2-CME-7-methoxy-DMAE NHS ester [ No CAS ]
  • [ 138529-46-1 ]
  • C42H51N6O11S(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In DMF (N,N-dimethyl-formamide); at 20℃; for 3h; Biotin-jeffamine (2.0 mg) and 2-CME-7-methoxy-DMAE NHS ester (0.5 mg) were dissolved in 0.50 ml of DMF, and the solution was stirred at room temperature over a period of three hours. After the solvents were removed under vacuum, the desired product was isolated from C-18 reversed phase chromatography and confirmed by MALDI-TOF mass spectrometry. (847.3 calc., 848.2 obs.)
  • 22
  • naphthofluorescein-NHS [ No CAS ]
  • [ 138529-46-1 ]
  • biotin-jeffamine-naphtofluorescein [ No CAS ]
YieldReaction ConditionsOperation in experiment
In DMF (N,N-dimethyl-formamide); at 20℃;Carbonate buffer; A solution of naphthofluorescein NHS ester (2.3 mg) in DMF (0.25 ml) was mixed with a solution of biotin-jeffamine (conjugate of biotin triethylene glycol diamine, 15 mg) in DMF (0.25 ml) and carbonate buffer (0.10 M, pH 8.5, 0.30 ml). After this mixture was stirred at room temperature overnight, solvents were removed under vacuum, and the residue was taken up in CH3CN/water for HPLC purification (C-18 reversed phase chromatography). The isolated product was identified by MALDI-TOF mass spectrometry. (833.2 calc., 833.5 obs.)
  • 23
  • C74H96N12O27S6Si3(4-)*4Na(1+) [ No CAS ]
  • [ 138529-46-1 ]
  • PC680-Biotin [ No CAS ]
  • 24
  • [ 929-59-9 ]
  • [ 58-85-5 ]
  • [ 138529-46-1 ]
YieldReaction ConditionsOperation in experiment
50% With triethylamine; isobutyl chloroformate; To a solution of biotin (3.0 g, 12.5 mmol) in DMF (100 ml) was added triethylamine (1.9 mL, 15 mmol) and the resulting mixture was stirred at the ice bath for half an hour, then slowly drops of isobutyl chloroformate (2.2 mL, 15 mmol) and the resulting mixture was stirred at the ice bath for 3 hour, then slowly drops of 2,2'-(Ethylenedioxy)bis(ethylamine) (3.7 mg, 22 mmol) and the resulting mixture was stirred at room temperature overnight. After removing DMF using a rotary evaporator, the residue was purified using silica gel column chromatography to give P6 as a white solid (3.5 g, 50% yield). 1H-NMR (400 MHz, DMSO-d6) delta (ppm): 8.909 (m, 1H), 6.35 (m, 2H), 4.27-4.24 (m, 1H), 4.10-4.09 (m, 1H), 3.58-3.33 (m, 9H), 3.24-3.03 (m, 5H), 2.92-2.89 (m, 2H), 2.17-2.14 (m, 2H), 1.56-1.26 (m, 7H). EI-MS (m/z) [M+H]+ 375.50.
In acetonitrile; Example 11 Synthesis of N-(8-amino-3,6-dioxaoctanyl)biotinamide 2,2'-(ethylenedioxy)bis(ethylamine) (21.1 g, 0.141 mol) was dissolved in dry acetonitrile (200 mL). Biotin TFP ester (2.8 g, 7.13 mmol) was dissolved in 450 mL dry acetonitrile at about 60 C. and added to the above solution after cooling to RT. The mixture was stirred at RT overnight. After the completion of the reaction (by TLC), the reaction mixture was concentrated and the residue was triturated with ether (300 mL) to afford a white solid. The crude product was further purified by column chromatography (silica gel, 60-120 mesh; eluent, chloroform:methanol, 2:8). Yield: 2.5 g (95%). 1H NMR (DMSO-d6) delta 7.8 (t, 1H), 6.4 (d, 2H), 4.4 (m, 1H), 4.2 (m, 1H), 3.0-3.4 (m, 11H), 2.8 (dd, 1H), 2.6 (m, 2H), 2.5 (d, 1H), 2.1(t, 2H), 1.4 (m, 4H), 1.3 (m, 4H). See Wilbur, D. S., Pathare, P. M., Hamlin, D. K., Weerawarna, S. A., Bioconjugate Chem. 1997, 8, 819-832.
  • 25
  • [ 5515-02-6 ]
  • [ 138529-46-1 ]
  • [ 1011268-29-3 ]
  • 26
  • [ 55183-45-4 ]
  • [ 138529-46-1 ]
  • [ 1011268-28-2 ]
  • 28
  • Nα-(tert-butoxycarbonyl)-1-methyl-L-tryptophan [ No CAS ]
  • [ 138529-46-1 ]
  • [ 1067667-78-0 ]
  • 29
  • C20H17F3N4O7S [ No CAS ]
  • [ 138529-46-1 ]
  • C36H45F3N8O10S2 [ No CAS ]
  • 30
  • C27H21F3N4O7S [ No CAS ]
  • [ 138529-46-1 ]
  • C43H49F3N8O10S2 [ No CAS ]
  • 31
  • [ 1116151-71-3 ]
  • [ 138529-46-1 ]
  • [ 1116151-72-4 ]
  • 32
  • [ 960149-32-0 ]
  • [ 138529-46-1 ]
  • [ 1092173-31-3 ]
  • 33
  • [ 1166232-53-6 ]
  • [ 138529-46-1 ]
  • [ 1166232-56-9 ]
  • 34
  • [ 1166232-70-7 ]
  • [ 138529-46-1 ]
  • [ 1166232-73-0 ]
  • 35
  • [ 1239744-72-9 ]
  • [ 138529-46-1 ]
  • [ 1361054-81-0 ]
  • 36
  • [ 1191419-15-4 ]
  • [ 138529-46-1 ]
  • [ 1191419-18-7 ]
  • 37
  • 16-mecapto-hexadecanoic acid N-hydroxysuccinimide [ No CAS ]
  • [ 138529-46-1 ]
  • [ 464189-53-5 ]
  • 38
  • [ 18523-48-3 ]
  • [ 138529-46-1 ]
  • [ 1263143-44-7 ]
  • 39
  • [ 1334110-94-9 ]
  • [ 138529-46-1 ]
  • [ 1334110-95-0 ]
YieldReaction ConditionsOperation in experiment
15% With 1-hydroxy-pyrrolidine-2,5-dione; 4-morpholineethanesulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20℃; for 12h;pH 5.5;Inert atmosphere; Compound 3 (20 mg, 0.038 mmol) was first incubated with EDC (9.6 mg, 0.05 mmol) and N-hydroxysuccinimide (5.7 mg, 0.05 mmol) in 50% MES buffer/acetonitrile (0.1 M, pH 5.5) for 20 min. Compound 6 (20 mg, 0.053 mmol)31 A. Spura, R.U. Riel, N.D. Freedman, S. Agrawal, C. Seto and E. Hawrot, J. Biol. Chem. 275 (2000), p. 22452. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (17)31 was then added and stirred under nitrogen for 12 h at room temperature after which it was concentrated to dryness under vacuum. The resulting residue was added to 50 mL of ethyl acetate and washed with saturated ammonium chloride and brine three times and then concentrated under vacuum. Purification by step gradient flash chromatography (5-8% methanol in dichloromethane) afforded 5 in 15% yield (5 mg, 0.006 mmol).
  • 40
  • [ 1334110-94-9 ]
  • [ 138529-46-1 ]
  • [ 1334110-96-1 ]
  • 41
  • [ 1352809-17-6 ]
  • [ 138529-46-1 ]
  • [ 1352809-18-7 ]
  • 42
  • [ 1352809-24-5 ]
  • [ 138529-46-1 ]
  • [ 1352809-19-8 ]
  • 43
  • C43H31F2N3O17 [ No CAS ]
  • [ 138529-46-1 ]
  • [ 1352809-20-1 ]
  • 44
  • C20H3F10N3O4 [ No CAS ]
  • [ 138529-46-1 ]
  • [ 1380335-11-4 ]
  • 45
  • [ 1160527-68-3 ]
  • [ 138529-46-1 ]
  • [ 1212057-35-6 ]
  • 46
  • [ 1227746-97-5 ]
  • [ 138529-46-1 ]
  • [ 1426246-95-8 ]
  • 47
  • [ 1426247-49-5 ]
  • [ 138529-46-1 ]
  • [ 1426247-01-9 ]
  • 48
  • [ 79463-77-7 ]
  • [ 138529-46-1 ]
  • C24H34N6O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
60 mg With triethylamine; In isopropyl alcohol; for 3h;Reflux; Sealed tube; A mixture of EZ-Link Amine Peg2 Biotin (82 mgs, 0.218 mmoles, Fisher Scientific,Pittsburgh, PA) 1, diphenyl N-cyanocarbonimidate (58 mgs, 1.1equiv) 2, triethylamine (65 ml, 2 equiv) in 3ml of anhydrous isopropanol was heated at reflux in a sealed tube for 3 hours.The reaction mixture was cooled, concentrated, and redissolved in CH2Cl2/Methanol(9:1,1 ml) and purified by tlc eluting with CH2Cl2/Methanol(9:1). Purification gave 60 mgs of a colorless film 3. NMR (CD3OD, 400 MHz): delta 7.1-7.5(m, 5H), 4.46 (m, 1H), 4.28 (m, 1H), 3.4-3.7 (m, 11H), 3.36 (m, 2H), 3.2 (m,1H), 2.9 (m, 1H) 2.68 (d, 1H),2.2 (m, 2H), 1.2-1.76 (m, 6H).
  • 49
  • [ 138529-46-1 ]
  • CC44 hydrochloride [ No CAS ]
  • 50
  • [ 138529-46-1 ]
  • CC46 [ No CAS ]
  • 51
  • [ 138529-46-1 ]
  • [ 121806-83-5 ]
  • [ 1559003-54-1 ]
  • 52
  • [ 132178-37-1 ]
  • [ 138529-46-1 ]
  • [ 1608127-20-3 ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine; In dichloromethane; for 19h; To a solution of biotin-PEG3- H2in dichloromethane (6 mL) was added triethylamine (54 mu., 39 mg, 0.39 mmol) and pent-4-ynoic acid succinimidyl ester (25 mg, 0.13 mmol). After 19 h, the reaction mixture was concentrated and the residue was purified via column chromatography (5?20% MeOH in DCM). The purified product was dissolved in DCM, filtered and concentrated, which yielded the desired product as a white solid (52 mg, 0.11 mmol, 85%).
  • 53
  • [ 1426827-91-9 ]
  • [ 138529-46-1 ]
  • [ 1638526-05-2 ]
  • 54
  • ubiquitin-<SUP>77</SUP>Asp [ No CAS ]
  • [ 138529-46-1 ]
  • ubiquitin-{biotinyl-{2-[2-(2-aminoethoxy)ethoxy]ethanamide}} [ No CAS ]
  • ubiquitin [ No CAS ]
  • 55
  • ubiquitin-CONHCH<SUB>2</SUB>CH=CH<SUB>2</SUB> [ No CAS ]
  • [ 138529-46-1 ]
  • ubiquitin-{biotinyl-{2-[2-(2-aminoethoxy)ethoxy]ethanamide}} [ No CAS ]
  • 56
  • C27H25NO11 [ No CAS ]
  • [ 138529-46-1 ]
  • C37H50N4O12S [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With dmap; triethylamine; In methanol; dichloromethane; at 20℃; Preparation of Compound 15 To a solution of biotin-amine (30 mg, 0.0802 mmol) in CH2CI2 (4 mL)/CH3OH (1 mL) was added compound 14 (20 mg, 0.037 mmol), followed by Et3N (11 0.0802 mmol) and DMAP (1 mg, 0.00802 mmol). The mixture was stirred at rt overnight. After that, the mixture was concentrated and purified by column chromatography to give compound 15 as a white solid (10 mg, 24 %). NMR (500 MHz, CDCI3) delta 6.41 (br s, 1H), 5.81 (br s, 1H), 5.54 (br s, 1H), 5.17 (br s, 1H), 4.98-4.69 (m, 2H), 4.49 (t, / = 4.9 Hz, 1H), 4.33 (t, / = 4.7 Hz, 1H), 4.10- 4.08 (m, 2H), 3.92 (d, / = 2.6 Hz, 1H), 3.62-3.55 (m, 8H), 3.49-3.43 (m, 3H), 3.42-3.36 (m, 2H), 3.19-3.14 (m, 1H), 2.92 (dd, / = 4.9, 12.9 Hz, 1H), 2.85-2.81 (m, 1H), 2.73 (d, / = 12.9 Hz, 1H), 2.39-2.35 (m, 1H), 2.27-2.08 (m, 4H), 2.04-1.95 (m, 2H), 1.77-1.51 (m, 8H), 1.49- 1.39 (m, 3H), 1.37-1.29 (m, 1H), 1.07 (s, 3H); 13C NMR (125 MHz) delta 197.3, 173.1, 173.0, 163.3, 159.4, 156.6, 125.8, 70.2, 70.0(4), 69.9(8), 69.9(1), 65.4, 64.1, 63.3, 61.8, 61.1, 60.8, 60.1, 56.2, 55.3, 55.3, 40.8, 40.6, 40.5, 39.2, 35.9, 35.4, 30.6, 29.7, 28.5, 28.1, 25.7, 25.5, 24.1, 23.2, 17.1, 13.9; LRMS (ESI) m/z 797.1 (M++Na).
  • 57
  • C27H25NO11 [ No CAS ]
  • [ 138529-46-1 ]
  • C37H52N4O12S [ No CAS ]
  • 58
  • [ 80366-85-4 ]
  • [ 76-05-1 ]
  • [ 138529-46-1 ]
  • N-(2-(2-(2-(2-(aminooxy)acetamido)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
30.7 mg Biotin derivative 4 (0.24 mmol, 115 mg) was dissolved in CH2Cl2/TFA (4:1) and stirred for 1 h. The mixture was concentrated and dried under vacuum. The residue was redissolved in dry DMF with compound 5 (0.48 mmol, 1.40 mg) and triethylamine (0.58 mmol, 58.9 mg) and stirred at room temperature overnight. Concentration and purification by column chromatography (CH2Cl2 + MeOH (slowly increasing from 0%to 7%); Rf(CH2Cl2:MeOH; 9:1) 0.3) yielded the Boc-protected product. The compound was then redissolved in CH2Cl2/TFA (4:1) and stirred for 1 h. The mixture was concentrated and dried under vaccum to yield the desired product 1 as TFA salt (1:1.16) in 22 % (53.0 mumol, 30.7 mg) as a white sticky solid.
  • 59
  • [ 35013-72-0 ]
  • [ 138529-46-1 ]
  • 60
  • [ 138529-46-1 ]
  • C37H52N6O7S [ No CAS ]
  • 61
  • [ 138529-46-1 ]
  • C42H58N8O8S [ No CAS ]
  • 62
  • [ 138529-46-1 ]
  • C27H48N8O6S [ No CAS ]
  • 63
  • [ 138529-46-1 ]
  • C38H60N8O8S [ No CAS ]
  • 64
  • [ 84624-27-1 ]
  • [ 138529-46-1 ]
  • C42H60N6O9S [ No CAS ]
  • 65
  • 1-(3-((2,5-dioxopyrrolidin-1-yl)oxy)-3-oxopropyl)-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate [ No CAS ]
  • [ 138529-46-1 ]
  • 1-(3,14-dioxo-18-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-7,10-dioxa-4,13-diazaoctadecyl)-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate [ No CAS ]
  • 66
  • [ 1030356-03-6 ]
  • [ 138529-46-1 ]
  • C59H52N4O13S7 [ No CAS ]
  • 67
  • C47H26O10S6 [ No CAS ]
  • [ 138529-46-1 ]
  • C63H54N4O13S7 [ No CAS ]
  • 68
  • C58H36N2O14S6 [ No CAS ]
  • [ 138529-46-1 ]
  • C90H92N10O20S8 [ No CAS ]
  • 69
  • [ 1293290-89-7 ]
  • [ 138529-46-1 ]
  • C63H54N4O13S7 [ No CAS ]
  • 70
  • sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate [ No CAS ]
  • [ 138529-46-1 ]
  • 4-(cyanoethynyl)-N-(2-(2-(2-(5-(3aS,4S,6aR)-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethoxy)ethoxy)ethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 3h; 4-(cyanoethynyl)-N-(2-(2-(2-(5-(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethoxy)ethoxy)ethyl)benzamide (37) (0317) (0318) To the solution of <strong>[138529-46-1]N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide</strong> (1 eq., 222 mg, 0.593 mmol) in dry DMF (1 mL) was added sodium 4-((4-(cyanoethynyl)benzoyl)oxy)-2,3,5,6-tetrafluorobenzenesulfonate (1.2 eq., 300 mg, 0.712 mmol) and DIEA (5.1 eq., 391 mg, 0.5 mL, 3.03 mmol). The mixture was stirred at r.t. for 3 hours and then purified by semi-preparative HPLC to give the desired product (68.8 mg, 0.13 mmol, 22% yield) as a yellow oil. (0319) 1H NMR (400 MHz, METHANOL-d4) delta=7.92 (d, J=8.5 Hz, 2 H), 7.81 (d, J=8.5 Hz, 2 H), 4.49 (dd, J=4.8, 7.8 Hz, 1 H), 4.30 (dd, J=4.5, 7.8 Hz, 1H), 3.71-3.56 (m, 8 H), 3.54 (t, J=5.5 Hz, 2H), 3.34 (t, J=5.5 Hz, 2H), 3.24-3.14 (m, 1H), 2.92 (dd, J=4.8, 12.8 Hz, 1H), 2.70 (d, J=12.8 Hz, 1H), 2.19 (t, J=7.4 Hz, 2H), 1.78-1.50 (m, 4H), 1.48-1.35 (m, 2H). (0320) 13C NMR (101 MHz, METHANOL-d4) delta=176.3, 168.8, 166.2, 138.9, 135.0, 129.1, 121.5, 105.9, 83.1, 71.5, 71.4, 70.7, 70.6, 64.6, 63.5, 61.8, 57.1, 41.2, 40.4, 36.9, 29.9, 29.6, 27.0.
  • 71
  • [ 1027338-09-5 ]
  • [ 138529-46-1 ]
  • carbonic acid 7,8-didehydro-1 ,2:5,6-dibenzocy-clooctene-3-yl ester, 8’-biotinylamine-3’, 6’-dioxaoc-tane 1’-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; To a solution of 8 (37 mg, 0.1 mmol) and NEt3 (30 mg, 0.3 mmol) in DMF (10 mL) was added 7 (39 mg, 0.1 mmol) under an atmosphere of Argon. After stirring the reaction mixture overnight at ambient temperature, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (CH2Cl2/CH3OH, 20/1, v/v) to afford 9 (44 mg, 71%). 1H NMR (500 MHz, CD3OD): delta 7.59 (1H, aromatics), 7.42-7.33 (7H, aromatics), 5.44, (1H, dd, J=5.0, 14.1 Hz, CHOH), 4.60, 4.46 (m, 2H, CHNH), 4.24 (s, 4H, OCH2CH2O), 3.72 (m, 4H, OCH2), 3.64 (m, 2H, CH2NH), 3.55 (m, 1H, CHS), 3.33 (dd, 1H, J1=12.0 Hz, J2=4.8 Hz, 1H, CHHexoS), 3.23 (t, 2H, J=6 Hz, CH2-NH2), 3.22, (1H, dd, J=5.0, 14.1 Hz, CH2), 2.88, (1H, dd, J=5.0, 14.1 Hz, CH2), 2.68 (d, 1H, J=12.45 Hz, CHHendoS), 2.20 (t, 2H, J=7.5 Hz, CH2CO), delta 1.4 (m, 6H, biotin-CH2). 13C NMR (75 MHz, CD3OD): delta 175.0, 164.9, 156.9, 152.5, 151.3, 129.9, 128.2, 128.1, 127.2, 127.1, 126.0, 125.7, 123.8, 121.2, 112.7, 109.8, 76.8, 70.2, 70.1, 69.8, 69.4, 62.1, 60.4, 55.8, 54.6, 46.0, 42.6, 40.6, 39.9, 39.1, 35.5, 28.6, 28.3, 25.6, 17.5, 16.1, 12.0; MALDI HRMS: m/z 643.2575 [M+Na+]. Calcd for C33H40N4NaO6S 643.2566.
  • 72
  • C56H91N5O25S [ No CAS ]
  • [ 138529-46-1 ]
  • C72H119N9O28S2 [ No CAS ]
  • 73
  • [ 334616-64-7 ]
  • [ 138529-46-1 ]
  • C41H58N6O9S [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Preparation of compound 67: To a solution of compound 66 (20 mg, 0.0445 mmol) in CH2C12 (2 mL) EDC (11 mg, 0.0579 mmol), HOBt (7.8 mg, 0.0579 mmol) and Et3N (8 mu, 0.0579 mmol) were added. The resulting mixture was stirred for 1 h. Compound 59 (25 mg, 0.0668 mmol) was predissolved in CH2CI2 (2 mL) and was added to the reaction mixture dropwisely. The reaction was stirred at room temperature for 1 day. When the reaction completed, the mixture was diluted with CH2C12 (2 mL), washed with 1 M HC1 (2 chi 2 mL), 1 M K2C03 (3 chi 2 mL) and brine ( 1 x 2 mL). The organic layer was dried over Na2SC>4, filtered and concentrated. The crude product was purified by flash chromatography (10% EtOH in CH2C12) to give purified product as yellow solid (24 mg, 62%). Analytical TLC (silica gel 60), 10% MeOH in CH2C12, R/= 0.35; NMR (300 MHz, CD3OD) delta 8.02 (d, / = 8.3 Hz, 2H), 7.85 (d, / = 8.3 Hz, 2H), 7.79 (d, / = 7.2 Hz, 2H), 7.67 (t, / = 7.4 Hz, 1H), 7.55 (t, / = 7.4 Hz, 2H), 4.56 (dd, / = 8.5, 5.6 Hz, 1H), 4.48 (dd, / = 7.5, 4.8 Hz, 1H), 4.28 (dd, / = 7.6, 4.6 Hz, 1H), 3.61-3.57 (m, 6H), 3.53 (t, / = 5.4 Hz, 2H), 3.42 (t, / = 5.4 Hz, 2H), 3.36-3.35 (m, 2H), 3.21-3.15 (m, 1H), 3.06 (t, / = 5.5 Hz, 2H), 2.90 (dd, / = 12.7, 4.9 Hz, 1H), 2.68 (d, / = 12.7 Hz, 1H), 2.20 (t, / = 7.4 Hz, 2H), 1.93-1.78 (m, 2H), 1.75-1.47 (m, 8H), 1.45-1.41 (m, 11H); 13C NMR (100 MHz, CD3OD) delta 197.7, 176.2, 176.1, 174.5, 169.2, 166.1, 141.5, 138.8, 138.4, 134.2, 131.1, 130.9, 129.7, 128.8, 79.8, 71.3, 70.6, 70.5, 63.4, 61.6, 57.0, 55.6, 41.0, 40.4, 40.3, 36.8, 32.8, 30.7, 30.6, 30.4, 29.8, 29.5, 28.8, 26.8, 24.4; IR (CH2C12) 3035, 2927, 2855, 1799, 1499, 1447 cm"1; LRMS (ESI) m/z 811.2 (M++H), 833.2 (M++Na); HRMS (ESI) calcd for C4iH59N609S (M++H) m/z 811.4064, found 811.4064.
  • 74
  • [ 138529-46-1 ]
  • C36H50N6O7S [ No CAS ]
  • 75
  • [ 138529-46-1 ]
  • C57H70N6O15S [ No CAS ]
  • 76
  • [ 929-59-9 ]
  • [ 35013-72-0 ]
  • [ 138529-46-1 ]
YieldReaction ConditionsOperation in experiment
Ca. 80% In acetonitrile; at 0 - 5℃;Inert atmosphere; 2. Synthesis of Biotin-Jeffamine intermediate (Scheme II) . 2, 2 '- (Ethylenedioxy) bis (ethylamine) (Sigma 385506, henceforth referred to as jeffamine) (0.9 mL, 5.8 mmol) was dissolved in 500 mL acetonitrile (MeCN, Sigma 34888) . Biotinyl-N-hydroxysuccinimide (B-NHS, 0.3 g, 0.88 mmol) was dissolved in MeCN (100 mL) , this solution was added into a dropping funnel. The B-NHS solution was then added dropwise to the jeffamine solution and stirred overnight, at 0-5 C under N2. The reaction was filtered, the solid washed with MeCN (2x 10 mL) and then with diethyl ether (2 x 10 mL) . Finally pulled dry under N2 to yield a white hygroscopic solid. TLC (10% MeOH/DCM + 5 dps NH4OH ) does not show apparent starting material after reaction. The solid was dissolved in MeOH (30 mL) at 40 C, dry, loaded on silica and eluted with 10 % MeOH/DCM + 1 % Et3N. Fractions 25-45 were collected and evaporated to a yellow solid/gel. Final yield: 0.257 g (~ 80% final efficiency) . This product is henceforth referred to as BJl .
  • 77
  • [ 530-62-1 ]
  • [ 138529-46-1 ]
  • C20H32N6O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 20℃; for 2.5h; Then, Bj 1 (0.017 g, 0.043 mmol) was dissolved in dry pyridine (5 mL, Sigma 270970) . CDI (Sigma 21860) was dissolved in the same volume of pyridine (0.074 g, 0.45 mmol) and added to the Bjl. The resulting solution was stirred for 2.5 hours at 20 C, when TLC revealed complete reaction (10% MeOH/DCM with 1% Et3N, Sigma T0886, Rf = 0.3) . The solvent was evaporated, the crude product was reconstituted in a minimum amount of DCM (Sigma 32222) and then ether was added in excess . The precipitate was collected and used in the next step without further purification. This product is henceforth referred to as BJ1'.
  • 78
  • [ 138529-46-1 ]
  • C46H71N13O13S [ No CAS ]
  • 79
  • 4-azidophthalic anhydride [ No CAS ]
  • [ 138529-46-1 ]
  • N-(2-(2-(2-(biotinylamino)ethoxy)ethoxy)ethyl)-4-azidophthalimide [ No CAS ]
  • 80
  • [ 6427-66-3 ]
  • [ 138529-46-1 ]
  • 4-azido-N-(2-(2-(2-(biotinylamino)ethoxy)ethoxy)ethyl)benzamide [ No CAS ]
  • 81
  • C30H20O8 [ No CAS ]
  • [ 138529-46-1 ]
  • C46H48N4O11S [ No CAS ]
  • 82
  • lysozyme chicken egg [ No CAS ]
  • [ 138529-46-1 ]
  • C65H107N19O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
This example demonstrates that Cu (Il)-mediated biotinylation after electrochemical peptide bond cleavage can be used to enrich spirolactone- containing peptides from proteins. Lysozyme (chicken egg), a protein of 14.6 kDa, was electrochemically cleaved at 2000 mV and the complex peptide mixture was biotinylated, enriched and subjected to nanoLC-MS/MS. Data were subjected to searching the chicken UniProt protein sequence database (Gallus gallus, updated 06-12-2016, SwissProt reviewed entries only) containing 2601 proteins. Modifications such as biotinylation (mass increment of 374.2062 Da) at the C-termini of predicted Tyr and Trp cleavage sites (resulting in an EC-Y+372.16 and an EC-W+388.18) were taken into account. (0093) The biotinylated peptide 54GILQINSRW62+388.18, which derives from the spirolactone-containing peptide 54GILQINSRW62+14, was identified as a unique sequence of lysozyme. The MS/MS spectrum of the doubly-charged precursor ion (m/z at 737.8960) shows the characteristic, abundant fragment ion of the coupled biotin tag at m/z 375.2062 together with Fragments 1 to 4, which are smaller fragments of the amine-PEG2-biotin tag providing a signature of a biotin-tagged compound (Figure 6).
  • 83
  • C17H21N3O4 [ No CAS ]
  • [ 138529-46-1 ]
  • LW-amine-PEG2-biotin [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(II) ion; In dimethyl sulfoxide; triethylamine; at 20℃; for 16h; As shown in Example 1, Cu (II) stabilized the spirolactone-containing peptide and prevented rearrangement to diketopiperazines without having to resort to acetylation. Consequently, the chemical coupling of LW+14 to hexylamine was studied in the absence and in the presence of Cu (II) in DMSO containing 0.1% TEA. Efficient chemical tagging was only observed in the presence of Cu (II) at a 50-fold molar excess of hexylamine (Figure 2). Reaction of LW+14 with amine-PEG2-biotin at a 200-fold molar excess was investigated next. Figures 3A and B show that only trace amounts of biotinylated LW+14 (Biotin-LW) were observed in the absence of Cu (II) ions since LW+14 underwent intramolecular rearrangement as the main reaction. Addition of Cu (II) prevented this side reaction resulting in complete biotinylation of LW+14 with amine-PEG2-biotin under otherwise identical conditions (Figures 3C and D). These results confirmed that addition of Cu (II) is critical for efficient chemical tagging of spirolactone- containing peptides.
  • 84
  • tert-butyl N-(4-((2,6-difluorophenyl)ethynyl)isoquinolin-1-yl)-N-methylglycinate [ No CAS ]
  • [ 138529-46-1 ]
  • N-(2-(4-((2,6-difluorophenyl)ethynyl)isoquinolin-1-yl)-4-oxo-8,11-dioxa-2,5-diazatridecan-13-yl)-5-((3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide [ No CAS ]
  • 85
  • [ 5961-85-3 ]
  • [ 138529-46-1 ]
  • C25H43N4O9PS [ No CAS ]
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 138529-46-1 ]

Ethers

Chemical Structure| 862373-14-6

[ 862373-14-6 ]

N-(2-(2-(2-Aminoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide hydrochloride

Similarity: 1.00

Chemical Structure| 359860-27-8

[ 359860-27-8 ]

N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Similarity: 1.00

Chemical Structure| 440680-87-5

[ 440680-87-5 ]

1,17-Bisbiotinylamino-3,6,9,12,15-pentaoxaheptadecane

Similarity: 1.00

Chemical Structure| 1205744-09-7

[ 1205744-09-7 ]

N-Ethyl-N-isopropylpropan-2-amine 5,21-dioxo-25-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-10,13,16-trioxa-6,20-diazapentacosanoate

Similarity: 0.85

Chemical Structure| 305372-39-8

[ 305372-39-8 ]

N-(2-(2-(2-(3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Similarity: 0.83

Amides

Chemical Structure| 862373-14-6

[ 862373-14-6 ]

N-(2-(2-(2-Aminoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide hydrochloride

Similarity: 1.00

Chemical Structure| 359860-27-8

[ 359860-27-8 ]

N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Similarity: 1.00

Chemical Structure| 440680-87-5

[ 440680-87-5 ]

1,17-Bisbiotinylamino-3,6,9,12,15-pentaoxaheptadecane

Similarity: 1.00

Chemical Structure| 65953-56-2

[ 65953-56-2 ]

N-(6-Aminohexyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Similarity: 0.86

Chemical Structure| 111822-45-8

[ 111822-45-8 ]

N-(2-Aminoethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide hydrochloride

Similarity: 0.86

Amines

Chemical Structure| 862373-14-6

[ 862373-14-6 ]

N-(2-(2-(2-Aminoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide hydrochloride

Similarity: 1.00

Chemical Structure| 359860-27-8

[ 359860-27-8 ]

N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Similarity: 1.00

Chemical Structure| 440680-87-5

[ 440680-87-5 ]

1,17-Bisbiotinylamino-3,6,9,12,15-pentaoxaheptadecane

Similarity: 1.00

Chemical Structure| 65953-56-2

[ 65953-56-2 ]

N-(6-Aminohexyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Similarity: 0.86

Chemical Structure| 111822-45-8

[ 111822-45-8 ]

N-(2-Aminoethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide hydrochloride

Similarity: 0.86

Related Parent Nucleus of
[ 138529-46-1 ]

Other Aliphatic Heterocycles

Chemical Structure| 862373-14-6

[ 862373-14-6 ]

N-(2-(2-(2-Aminoethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide hydrochloride

Similarity: 1.00

Chemical Structure| 359860-27-8

[ 359860-27-8 ]

N-(2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Similarity: 1.00

Chemical Structure| 440680-87-5

[ 440680-87-5 ]

1,17-Bisbiotinylamino-3,6,9,12,15-pentaoxaheptadecane

Similarity: 1.00

Chemical Structure| 65953-56-2

[ 65953-56-2 ]

N-(6-Aminohexyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Similarity: 0.86

Chemical Structure| 111822-45-8

[ 111822-45-8 ]

N-(2-Aminoethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide hydrochloride

Similarity: 0.86