Fmoc- ß-HoIle-OH

CAS# 193954-27-7

Fmoc- ß-HoIle-OH

Catalog No. BCC3237----Order now to get a substantial discount!

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Chemical structure

Fmoc- ß-HoIle-OH

3D structure

Chemical Properties of Fmoc- ß-HoIle-OH

Cas No. 193954-27-7 SDF Download SDF
PubChem ID 2761523 Appearance Powder
Formula C22H25NO4 M.Wt 367.4
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3R,4R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylhexanoic acid
SMILES CCC(C)C(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
Standard InChIKey VHZUUIWBAYOCDD-JLTOFOAXSA-N
Standard InChI InChI=1S/C22H25NO4/c1-3-14(2)20(12-21(24)25)23-22(26)27-13-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,14,19-20H,3,12-13H2,1-2H3,(H,23,26)(H,24,25)/t14-,20-/m1/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.

Fmoc- ß-HoIle-OH Dilution Calculator

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Fmoc- ß-HoIle-OH Molarity Calculator

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Preparing Stock Solutions of Fmoc- ß-HoIle-OH

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7218 mL 13.6091 mL 27.2183 mL 54.4366 mL 68.0457 mL
5 mM 0.5444 mL 2.7218 mL 5.4437 mL 10.8873 mL 13.6091 mL
10 mM 0.2722 mL 1.3609 mL 2.7218 mL 5.4437 mL 6.8046 mL
50 mM 0.0544 mL 0.2722 mL 0.5444 mL 1.0887 mL 1.3609 mL
100 mM 0.0272 mL 0.1361 mL 0.2722 mL 0.5444 mL 0.6805 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 Fmoc- ß-HoIle-OH

Fast and Facile Synthesis of 4-Nitrophenyl 2-Azidoethylcarbamate Derivatives from N-Fmoc-Protected alpha-Amino Acids as Activated Building Blocks for Urea Moiety-Containing Compound Library.[Pubmed:28055180]

ACS Comb Sci. 2017 Mar 13;19(3):131-136.

A fast and facile synthesis of a series of 4-nitrophenyl 2-azidoethylcarbamate derivatives as activated urea building blocks was developed. The N-Fmoc-protected 2-aminoethyl mesylates derived from various commercially available N-Fmoc-protected alpha-amino acids, including those having functionalized side chains with acid-labile protective groups, were directly transformed into 4-nitrophenyl 2-azidoethylcarbamate derivatives in 1 h via a one-pot two-step reaction. These urea building blocks were utilized for the preparation of a series of urea moiety-containing mitoxantrone-amino acid conjugates in 75-92% yields and parallel solution-phase synthesis of a urea compound library consisted of 30 members in 38-70% total yields.

Ultrashort self-assembling Fmoc-peptide gelators for anti-infective biomaterial applications.[Pubmed:28066954]

J Pept Sci. 2017 Feb;23(2):131-140.

Biomaterial-related infections have a significant impact on society and are a major contributor to the growing threat of antimicrobial resistance. Current licensed antibiotic classes struggle to breakdown or penetrate the exopolysaccharide biofilm barrier, resulting in sub-therapeutic concentrations of antibiotic at the surface of the biomaterial, treatment failure and increased spread of resistant isolates. This paper focuses for the first time on the ability of ultrashort Fmoc-peptide gelators to eradicate established bacterial biofilms implicated in a variety of medical device infections (Gram-positive: Staphylococcus aureus, Staphylococcus epidermidis and Gram-negative Escherichia coli, Pseudomonas aeruginosa). The effect of increasing the cationicity of FmocFF via addition of di-lysine and di-orntithine was also studied with regard to antibacterial activity. Our studies demonstrated that Fmoc-peptides (FmocFF, FmocFFKK, FmocFFFKK, FmocFFOO) formed surfactant-like soft gels at concentrations of 1% w/v and above using a method of glucono-delta-Lactone pH induction. The majority of Fmoc-peptides (0.5-2% w/v) demonstrated selective action against established (grown for 24 h) biofilms of Gram-positive and Gram-negative pathogens. These results are likely to increase the clinical translation of short-peptide gelator platforms within the area of anti-infective biomaterials including as wound dressings and coatings for prostheses, catheters, heart valves and surgical tubes. In the long term, this will lead to wider treatment choices for clinicians and patients involved in the management of medical device infections and reduce the burden of antimicrobial resistance. Copyright (c) 2017 European Peptide Society and John Wiley & Sons, Ltd.

Scope and Limitations of Fmoc Chemistry SPPS-Based Approaches to the Total Synthesis of Insulin Lispro via Ester Insulin.[Pubmed:27905149]

Chemistry. 2017 Jan 31;23(7):1709-1716.

We have systematically explored three approaches based on 9-fluorenylmethoxycarbonyl (Fmoc) chemistry solid phase peptide synthesis (SPPS) for the total chemical synthesis of the key depsipeptide intermediate for the efficient total chemical synthesis of insulin. The approaches used were: stepwise Fmoc chemistry SPPS; the "hybrid method", in which maximally protected peptide segments made by Fmoc chemistry SPPS are condensed in solution; and, native chemical ligation using peptide-thioester segments generated by Fmoc chemistry SPPS. A key building block in all three approaches was a Glu[O-beta-(Thr)] ester-linked dipeptide equipped with a set of orthogonal protecting groups compatible with Fmoc chemistry SPPS. The most effective method for the preparation of the 51 residue ester-linked polypeptide chain of ester insulin was the use of unprotected peptide-thioester segments, prepared from peptide-hydrazides synthesized by Fmoc chemistry SPPS, and condensed by native chemical ligation. High-resolution X-ray crystallography confirmed the disulfide pairings and three-dimensional structure of synthetic insulin lispro prepared from ester insulin lispro by this route. Further optimization of these pilot studies could yield an efficient total chemical synthesis of insulin lispro (Humalog) based on peptide synthesis by Fmoc chemistry SPPS.

Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides.[Pubmed:28120383]

J Pept Sci. 2017 Mar;23(3):202-214.

The rise of CuI-catalyzed click chemistry has initiated an increased demand for azido and alkyne derivatives of amino acid as precursors for the synthesis of clicked peptides. However, the use of azido and alkyne amino acids in peptide chemistry is complicated by their high cost. For this reason, we investigated the possibility of the in-house preparation of a set of five Fmoc azido amino acids: beta-azido l-alanine and d-alanine, gamma-azido l-homoalanine, delta-azido l-ornithine and omega-azido l-lysine. We investigated several reaction pathways described in the literature, suggested several improvements and proposed several alternative routes for the synthesis of these compounds in high purity. Here, we demonstrate that multigram quantities of these Fmoc azido amino acids can be prepared within a week or two and at user-friendly costs. We also incorporated these azido amino acids into several model tripeptides, and we observed the formation of a new elimination product of the azido moiety upon conditions of prolonged couplings with 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate/DIPEA. We hope that our detailed synthetic protocols will inspire some peptide chemists to prepare these Fmoc azido acids in their laboratories and will assist them in avoiding the too extensive costs of azidopeptide syntheses. Experimental procedures and/or analytical data for compounds 3-5, 20, 25, 26, 30 and 43-47 are provided in the supporting information. (c) 2017 The Authors Journal of Peptide Science published by European Peptide Society and John Wiley & Sons Ltd.

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