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Chemical Structure| 203866-19-7 Chemical Structure| 203866-19-7

Structure of Fmoc-cis-4-F-Pro-OH
CAS No.: 203866-19-7

Chemical Structure| 203866-19-7

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Product Details of [ 203866-19-7 ]

CAS No. :203866-19-7
Formula : C20H18FNO4
M.W : 355.36
SMILES Code : O=C(O)[C@H]1N(C(OCC2C3=CC=CC=C3C4=CC=CC=C24)=O)C[C@@H](F)C1
MDL No. :MFCD07781261
InChI Key :CJEQUGHYFSTTQT-SGTLLEGYSA-N
Pubchem ID :2756199

Safety of [ 203866-19-7 ]

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

Application In Synthesis of [ 203866-19-7 ]

* 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 [ 203866-19-7 ]

[ 203866-19-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 455-40-3 ]
  • Fmoc-Dab(Alloc)–OH [ No CAS ]
  • [ 138775-22-1 ]
  • [ 142-62-1 ]
  • [ 203866-19-7 ]
  • hexanoyl-(cis-4-fluoro-L-proline)-NMeIle-Dab(3,5diFBz)-NHOH [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% General procedure: The compounds were synthesized manually by SPPS following theFmoc/tert-butyl (Fmoc/tBu) strategy and using 2-chlorotrityl resin (IrisBiotech) in polypropylene syringes, each fitted with a polyethyleneporous disk. Solvents and soluble reagents were removed by suction.Prior to starting the synthesis, the resin was conditioned by swelling indichloromethane (DCM, 15 min) and washings with dimethylformamide(DMF, 3×30 s). The incorporation of hydroxylamine linker wasperformed by adding N-Fmoc-hydroxylamine (1.5 eq) and N,N-diisopropylethylamine(10 eq) to the resin in DCM for 24 h [50]. After this,the unreacted points of the resin were capped with methanol (0.8 mL/ gresin, 10 min). The Fmoc protecting groups were removed using 20%piperidine (Carlo Erba) solution in DMF (Carlo Erba) (2x1 min, 1x10min). The coupling reactions were performed in DMF using Fmocaminoacids (3 eq) and oxyma pure (3 eq, Iris Biotech) in the presenceof diisopropylcarbodiimide (3 eq) for 90 min. This mixture is known toproduce couplings with high efficiency and extremely low or null racemization[51]. The reaction was monitored by colorimetric tests: theKaiser colorimetric test [52] was used for the detection of primaryamines, while the chloranil test was used for secondary amines boundto the solid-phase [53]. The Alloc group was removed by adding phenylsilane(10 eq) and Pd(PPh3)4 (0.1 eq) in DCM (3×15 min). Peptideswere cleaved from the resin using 30% trifluoroacetic acid (TFA,Fluorochem) in DCM (3×15 min). After cleavage, filtrates and DCMwashes (3×5 min) were evaporated and lyophilized. The crude productobtained was purified by reverse-phase column chromatographyusing a Combi flash ISCO RF provided with dual ultraviolet detectionusing a high performance RediSep Rf Gold C18 column (Teledyne isco).The purity of the purified compounds was determined at lambda=220 nmby analytical HPLC (Waters Alliance 2695 separation module equippedwith a 2487 photodiode array detector, a Sunfire C18 column(100×4.6mm×5 mum, 100 A, Waters), and Empower software). Flowrate 1 mL/min, mobile phase H2O (0.036% TFA) and acetonitrile(0.045% TFA). Compound identity was assessed by analytical HPLC-MS(Waters Alliance 2695 separation module system equipped with aWaters 2998 photodiode array detector electrospray ionization (ESI)-MS micromass ZQ and a Sunfire C18 column (2.1×100mm×3.5 mum,100 A, Waters), and Masslynx software. Flow rate 0.3 mL/min, mobilephase H2O (0.1% formic acid (FA)) and acetonitrile (0.07% FA). Thepurity of all final compounds was 95% or higher, as measured by HPLC.The exact mass for compound 40 was measured in a LCT-Premier XE(Waters-Micromass) coupled to UPLC (Acquity, Waters).
  • 2
  • polyethylene glycol polyamide resin [ No CAS ]
  • [ 908846-88-8 ]
  • [ 90711-56-1 ]
  • (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)amino)methyl)phenyl)propanoic acid [ No CAS ]
  • [ 71989-35-0 ]
  • [ 35661-38-2 ]
  • [ 77128-72-4 ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 203866-19-7 ]
  • C79H95F3N13O15Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/iBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. The sequence of Fmoc protected amino acids and building blocks used were: ? (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(((1-(4,4-dimethyl-2,6- dioxocyclohexylidene)ethyl)amino)methyl)phenyl)propanoic acid ? (S)-1 -(((9H-fluoren-9-yl)methoxy)carbonyl)-2-methylpyrrolidine-2-carboxylic acid ? (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid ? N-(((9H-fluoren-9-yl)methoxy)carbonyl)-0-(tert-butyl)-L-threonine ? (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid ? (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid ? (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid ? (((9H-fluoren-9-yl)methoxy)carbonyl)-D-alanine ? N-Allyloxycarbonyl glycine
 

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