Fmoc-Cys(Trt)-OH

Base Information

• Chemical Name: Fmoc-Cys(Trt)-OH
• CAS No.: 103213-32-7
• Molecular Formula: C37H31NO4S
• Molecular Weight: 585.723
• Hs Code.: 29309090
• European Community (EC) Number: 600-408-4
• DSSTox Substance ID: DTXSID70145699
• Nikkaji Number: J1.565.797I
• Wikidata: Q72479025
• ChEMBL ID: CHEMBL396414
• Mol file: 103213-32-7.mol

Synonyms:Fmoc-S-trityl-Cys;N-(alpha)-fluorenylmethyloxycarbonyl-S-tritylcysteine

Chemical Property of Fmoc-Cys(Trt)-OH

Chemical Property:

• Appearance/Colour: white to light yellow crystal powde
• Vapor Pressure: 1.68E-24mmHg at 25°C
• Melting Point: 172-177 °C
• Refractive Index: 18 ° (C=1, THF)
• Boiling Point: 763.4 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 415.5 °C
• PSA: 100.93000
• Density: 1.27 g/cm³
• LogP: 8.09450
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water. Soluble in most organic solvents.
• XLogP3: 8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 585.19737964
• Heavy Atom Count: 43
• Complexity: 841

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-Cys(Trt)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SCC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
• Isomeric SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SC[C@@H](C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
• Uses: It is potentially useful for proteomics studies, and solid phase peptide synthesis techniques. Cysteine is versatile amino acid involved with many biological processes, including the formation of disulfide bonds - a critical component of protein structure. This compound could be useful as an unusual amino acid analog to aid in the deconvolution of protein structure and function. Fmoc-Cys(Trt)-OH is an N-terminal protected cysteine derivative used in peptide synthesis. Some of the examples are:Synthesis of mono- and bi-functionalized platinum(IV) complexes to target angiogenic tumor vasculature.Synthesis of proteins through native chemical ligation of peptide hydrazides as thioester surrogates via solid-phase synthesis.Synthesis of glycoconjugates by conjugating reducing sugars to cysteine residues of peptides.

Technology Process of Fmoc-Cys(Trt)-OH

There total 8 articles about Fmoc-Cys(Trt)-OH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

S-trityl-L-cysteine (2799-07-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4)

Guidance literature:

With sodium carbonate; In water; acetonitrile;

DOI:10.1021/acs.orglett.0c03850

Reference yield:

trityl chloride (76-83-5) → N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl-formamide / 48 h / 20 °C

2: sodium carbonate / water; acetonitrile

With sodium carbonate; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.0c03850

Reference yield:

L-Cys(trt)-OH dicyclohexylamine salt + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4)

Guidance literature:

L-Cys(trt)-OH dicyclohexylamine salt; N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium carbonate; In water; acetonitrile; at 0 - 20 ℃; pH=8;

With potassium hydrogensulfate; In water; acetonitrile; pH=2 - 3;

DOI:10.1080/00397910802632563

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

trityl chloride

N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine

N,N'-bis[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cystine

Downstream raw materials:

(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionic acid 4-(2,4-dichloro-phenoxycarbonylmethoxy)-benzyl ester

N^α-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl ester

Fmoc-Cys(Trt)-OMe

Refernces

• 1、 De La Fuente, M. Carmen,Jiménez, Carlos,Rodríguez, Jaime,Segade, Yuri,Valderrama, Katherine. "Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+Complex". supporting information. p. 340 - 345. Retrieved 2021/01/13.
• 2、 Nowshuddin, Shaik,Rao,Reddy, A. Ram. "Efficient procedure for the preparation of oligomer-free N-fmoc amino acids". experimental part. p. 2022 - 2031. Retrieved 2009/11/30.