Boc-Phe-OH

CAS# 13734-34-4

Boc-Phe-OH

Catalog No. BCC3432----Order now to get a substantial discount!

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Chemical structure

Boc-Phe-OH

3D structure

Chemical Properties of Boc-Phe-OH

Cas No. 13734-34-4 SDF Download SDF
PubChem ID 77857 Appearance Powder
Formula C14H19NO4 M.Wt 265.3
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Boc-L-Phenylalanine
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid
SMILES CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(=O)O
Standard InChIKey ZYJPUMXJBDHSIF-NSHDSACASA-N
Standard InChI InChI=1S/C14H19NO4/c1-14(2,3)19-13(18)15-11(12(16)17)9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/t11-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Boc-Phe-OH Dilution Calculator

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Boc-Phe-OH Molarity Calculator

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Preparing Stock Solutions of Boc-Phe-OH

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.7693 mL 18.8466 mL 37.6932 mL 75.3864 mL 94.2329 mL
5 mM 0.7539 mL 3.7693 mL 7.5386 mL 15.0773 mL 18.8466 mL
10 mM 0.3769 mL 1.8847 mL 3.7693 mL 7.5386 mL 9.4233 mL
50 mM 0.0754 mL 0.3769 mL 0.7539 mL 1.5077 mL 1.8847 mL
100 mM 0.0377 mL 0.1885 mL 0.3769 mL 0.7539 mL 0.9423 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Boc-Phe-OH

Synthesis of different types of dipeptide building units containing N- or C-terminal arginine for the assembly of backbone cyclic peptides.[Pubmed:10888199]

J Pept Res. 2000 Jun;55(6):428-35.

Different types of dipeptide building units containing N- or C-terminal arginine were prepared for synthesis of the backbone cyclic analogues of the peptide hormone bradykinin (BK: Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg). For cyclization in the N-terminal sequence N-carboxyalkyl and N-aminoalkyl functionalized dipeptide building units were synthesized. In order to avoid lactam formation during the condensation of the N-terminal arginine to the N-alkylated amino acids at position 2, the guanidino function has to be deprotected. The best results were obtained by coupling Z-Arg(Z)2-OH with TFFH/collidine in DCM. Another dipeptide building unit with an acylated reduced peptide bond containing C-terminal arginine was prepared to synthesize BK-analogues with backbone cyclization in the C-terminus. To achieve complete condensation to the resin and to avoid side reactions during activation of the arginine residue, this dipeptide unit was formed on a hydroxycrotonic acid linker. HYCRAM technology was applied using the Boc-Arg(Alloc)2-OH derivative and the Fmoc group to protect the aminoalkyl function. The reduced peptide bond was prepared by reductive alkylation of the arginine derivative with the Boc-protected amino aldehyde, derived from Boc-Phe-OH. The best results for condensation of the branching chain to the reduced peptide bond were obtained using mixed anhydrides. Both types of dipeptide building units can be used in solid-phase synthesis in the same manner as amino acid derivatives.

Enhancement of peptide coupling reactions by 4-dimethylaminopyridine.[Pubmed:7341528]

Int J Pept Protein Res. 1981 Nov;18(5):459-67.

4-Dimethylaminopyridine (DMAP) was found to be useful in the enhancement of peptide coupling reactions mediated by dicyclohexylcarbodiimide or symmetrical anhydrides. In an automated synthesis of the model heptapeptide Boc-Ala-Cle-Ile-Val-Pro-Arg(Tos)-Gly-OCH2-Resin (Cle, cycloleucine), the efficiencies of various coupling methods such as dicyclohexylcarbodiimide, dicyclohexylcarbodiimide plus 1-hydroxybenzotriazole, and symmetrical anhydride were compared with that of dicyclohexylcarbodiimide plus 4-dimethylaminopyridine. Based on the amino acid composition of the peptide-resin samples and high pressure liquid chromatographic analyses of the protected heptapeptide amide obtained from the ammonolytic cleavage of the peptide-resin samples, it was concluded that only dicyclohexylcarbodiimide plus 4-dimethylaminopyridine gave the desired near quantitative couplings in those cycles involving the sterically hindered amino acid residues. Observations were also made that 4-dimethylaminopyridine was a useful additive in a modified symmetrical anhydride method of coupling. In the synthesis of the model tetrapeptide Leu-Ala-Gly-Val on a Pam resin, the anhydride couplings were accelerated by DMAP and the product was equivalent in homogeneity to that obtained by the best previous methods. In addition, no racemization was detectable by a sensitive chromatographic method. There also was no detectable racemization found in a DCC-DMAP coupling of Boc-Ile-OH with H-Val-OCH2-resin. However, significant racemization was observed during the coupling of Boc-Phe-OH with H-Glu(OBzl)-OCH2-resin. DMAP is recommended as an additive for coupling hindered amino acids, particularly C alpha-substituted residues, where little or no racemization is expected.

Evaluation of carbodiimides using a competition method.[Pubmed:9230479]

J Pept Sci. 1997 Mar-Apr;3(2):141-4.

A competitive reaction of activated Boc-Ala-OH and Boc-Phe-OH with H-Leu-resin has been developed for assessing the relative efficiencies of different carbodiimides. This allowed a comparison of the efficiency of the carbodiimides N,N'-dicyclohexylcarbodiimide,N,N'-diisopropylcarbodiimide, N-tert-butyl-N'-methylcarbodiimide and N-tert-butyl-N'-ethylcarbodiimide. Comparable results were obtained when these reagents were used for the preformation of symmetrical anhydrides or of 1-hydroxybenzotriazole esters in situ. Differential incorporation was observed when asymmetrical carbodiimides were used for peptide bond formation by the direct carbodiimide procedure.

Mixed (phthalocyaninato)(porphyrinato) rare earth double-decker complexes with C4 chirality: synthesis, resolution, and absolute configuration assignment.[Pubmed:19689128]

Inorg Chem. 2009 Sep 21;48(18):8925-33.

Mixed (phthalocyaninato)(porphyrinato) rare earth double-decker complexes [HM(III){Pc(alpha-3-OC(5)H(11))(4)}{TOAPP}] [Pc(alpha-3-OC(5)H(11))(4) = 1,8,15,22-tetrakis(3-pentyloxy)-phthalocyaninate; TOAPP = meso-tetrakis(4-octylamino-phenyl)porphyrinate; M = Y (1), Ho (2)] were prepared as a racemic mixture by treating metal-free phthalocyanine H(2)Pc(alpha-3-OC(5)H(11))(4) with half-sandwich complexes [M(III)(acac)(TOAPP)], generated in situ from M(acac)(3).nH(2)O and H(2)TAPP [TAPP = meso-tetrakis(4-amino-phenyl)porphyrinate], in refluxing 1-octanol. The obtained double-deckers were characterized by elemental analysis and various spectroscopic methods. The molecular structures of 1 and 2 were determined by single-crystal X-ray diffraction analysis. The compounds crystallize in the triclinic system with a pair of enantiomeric double-deckers per unit cell. Resolution of 1 and 2 was achieved using a chiral HPLC technique combined with the formation of their diastereomeric mixture using L-Boc-Phe-OH as the chiral resolving agent, yielding for the first time the pure diastereoisomers of chiral mixed (phthalocyaninato)(porphyrinato) rare earth double-decker complexes with C(4) symmetry. The absolute configuration of these chiral complexes was assigned by comparing the experimental circular dichroism spectrum with a simulated one on the basis of time-dependent density functional theory calculations.

N-urethane-protected amino alkyl isothiocyanates: synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides.[Pubmed:19537728]

J Org Chem. 2009 Aug 7;74(15):5260-6.

Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).

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