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Chemical Structure| 123417-18-5 Chemical Structure| 123417-18-5

Structure of Boc-Glu(Ofm)-OH
CAS No.: 123417-18-5

Chemical Structure| 123417-18-5

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Product Details of [ 123417-18-5 ]

CAS No. :123417-18-5
Formula : C24H27NO6
M.W : 425.47
SMILES Code : O=C(O)[C@@H](NC(OC(C)(C)C)=O)CCC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O
MDL No. :MFCD00076934
InChI Key :RCQRXYWDDVULAP-FQEVSTJZSA-N
Pubchem ID :129966

Safety of [ 123417-18-5 ]

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

Application In Synthesis of [ 123417-18-5 ]

* 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 [ 123417-18-5 ]

[ 123417-18-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 13734-41-3 ]
  • [ 13139-15-6 ]
  • [ 15761-38-3 ]
  • [ 2488-15-5 ]
  • [ 13734-34-4 ]
  • [ 15260-10-3 ]
  • [ 13836-37-8 ]
  • [ 23680-31-1 ]
  • [ 73821-95-1 ]
  • [ 123417-18-5 ]
  • [ 84624-27-1 ]
  • [ 47689-67-8 ]
  • [ 47355-10-2 ]
  • [ 83468-83-1 ]
  • [ 65420-40-8 ]
  • [ 98115-14-1 ]
  • HSQGTFTSDYSKYLDERRAQDFVQWLMNT-NH2, lactam 12-16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 11 Synthesis of Glucagon Lactams (0299) 285 mg (0.2 mmole) methoxybenzhydrylamine resin (Midwest Biotech) was added to a 60 mL reaction vessels and the following sequence was assembled on a modified Applied Biosystems 430A peptide synthesizer using Boc DEPBT-activated single couplings. HSQGTFTSDYSKYLDERRAQDFVQWLMNT-NH2 (12-16 Lactam; SEQ ID NO: 12) (0300) The following side chain protecting groups were used: Arg(Tos), Asp(OcHx), Asn(Xan), Glu(OFm), His(BOM), Lys(Fmoc), Ser(Bzl), Thr(Bzl), Trp(CHO), Tyr(Br-Z). Lys(Cl-Z) was used at position 12 if lactams were constructed from 16-20, 20-24, or 24-28. The completed peptidyl resin was treated with 20% piperidine/dimethylformamide for one hour with rotation to remove the Trp formyl group as well as the Fmoc and OFm protection from Lys12 and Glu16. Upon confirmation of removal by a positive ninhydrin test, the resin was washed with dimethylformamide, followed by dichloromethane and than again with dimethylformamide. The resin was treated with 520 mg (1 mmole) Benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOP) in dimethylformamide and diisopropylethylamine (DIEA). The reaction proceeded for 8-10 hours and the cyclization was confirmed by a negative ninhydrin reaction. The resin was washed with dimethylformamide, followed by dichloromethane and subsequently treated with trifluoroacetic acid for 10 minutes. The removal of the Boc group was confirmed by a positive ninhydrin reaction. The resin was washed with dimethylformamide and dichloromethane and dried before being transferred to a hydrofluoric acid (HF) reaction vessel. 500 muL p-cresol was added along with a magnetic stir bar. The vessel was attached to the HF apparatus (Peninsula Labs), cooled in a dry ice/methanol bath, evacuated, and approximately 10 mL of liquid hydrofluoric acid was condensed into the vessel. The reaction was stirred for 1 hour in an ice bath and the HF was subsequently removed in vacuo. The residue was suspended in ethyl ether; the solids were filtered, washed with ether, and the peptide was solubilized with 150 mL 20% acetonitrile/1% acetic acid. (0301) An analytical HPLC analysis of the crude solubilized peptide was conducted under the following conditions [4.6 X 30 mm Xterra C8, 1.50 mL/min, 220 nm, A buffer 0.1% TFA/10% ACN, B buffer 0.1% TFA/100% ACN, gradient 5-95%B over 15 minutes]. The extract was diluted twofold with water and loaded onto a 2.2 X 25 cm Vydac C4 preparative reverse phase column and eluted using an acetonitrile gradient on a Waters HPLC system (A buffer of 0.1% TFA/10% ACN, B buffer of 0.1% TFA/10% CAN and a gradient of 0-100% B over 120 minutes at a flow of 15.00 ml/min. HPLC analysis of the purified peptide demonstrated greater than 95% purity and electrospray ionization mass spectral analysis confirmed a mass of 3506 Da for the 12-16 lactam. Lactams from 16-20, 20-24, and 24-28 were prepared similarly.
 

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