N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine (HCID 128239)

Overview

side chain protected amino acid; structure given in first source

Names & identifiers

Preferred name: N-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteine
IUPAC: (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanylpropanoic acid
English name: FMOC-S-trityl-L-cysteine
Molecular formula: C37H31NO4S
Molecular weight: 585.71

Names & synonyms

103213-32-7Fmoc-L-Cys(Trt)-OHFmoc-S-trityl-cysN(alpha)-Fluorenylmethyloxycarbonyl-S-tritylcysteine7VS47T4LL8DTXSID70145699N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-(triphenylmethyl)-L-cysteineN-(alpha)-fluorenylmethyloxycarbonyl-S-tritylcysteineN-((9H-Fluoren-9-ylmethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteineRefChem:821415DTXCID1068190Fmoc-Cys(Trt)-OH

Show more names

FMOC-CYS(TRT)Fomc-Cys(Trt)-OHFmoc-Cyc(Trt)-OHFMOC-L-CYS(TRT)Fmoc-Cys(Trt)-0HFmoc-Cys(Trt)-OH Fmoc-Cys(Trt)-OH

FMOC-S-trityl-L-cysteineN-Fmoc-S-trityl-L-cysteineMFCD00038538(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanylpropanoic acidCHEMBL396414L-Cysteine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-S-(triphenylmethyl)-M03395(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-[(triphenylmethyl)sulfanyl]propanoic acid

Database identifiers

CAS: 103213-32-7
PubChem CID: 128239
DTXSID: DTXSID70145699
ChEMBL: CHEMBL396414
UNII: 7VS47T4LL8
EC Number: 600-408-4
Nikkaji: J1.565.797I

Properties

Computed structural properties

XLogP: 8
Topological polar surface area: 101 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 11
Heavy atoms: 43
Formal charge: 0
Complexity: 841

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives

Physical DescriptionBeige powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point: 170 · 170-173 °C(lit.)
alpha: 16 · 16 º (c=1, THF)
Boiling point: 763.4 · 763.4±60.0 °C(Predicted)
Density: 1.27 · 1.270±0.06 g/cm3(Predicted)
refractive index: 18 ° · 18 ° (C=1, THF)
storage temp.: 2 · 2-8°C
solubility: Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
pka: 3.7 · 3.70±0.10(Predicted)
form: Powder
color: White to almost white
optical activity: 20 · [α]20/D +16.0±2°, c = 1% in THF
Water Solubility: Insoluble in water. Soluble in most organic solvents.
BRN: 4221286 · 4221286
Major Application: peptide synthesis
InChIKey: KLBPUVPNPAJWHZ-UMSFTDKQSA-N
SMILES: OC(=O)[C@H](CSC(c1ccccc1)(c2ccccc2)c3ccccc3)NC(=O)OCC4c5ccccc5-c6ccccc46
CAS DataBase Reference: 103213 · 103213-32-7(CAS DataBase Reference)
UNSPSC Code: 12352209 · 12352209
NACRES: 26 · NA.26
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 22 · 22-24/25-26
WGK Germany: 3 · 3
F: 9 · 9-21
Hazard Note: Irritant
HS Code: 29309090 · 29309090
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 42.9% (3 of 7) of reports.

Warning

H302 (14.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 7 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesSkin Irrit. 2 (57.1%)

Safety data

F: 9-21
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29309090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 22-24/25-26
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
REACH Registrations: Active
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Uses & manufacturing

UsesSide chain protected amino acid. [ChemIDplus]

Applications · 3 items

UsesFmoc-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.

UsesFMOC-S-trityl-L-cysteine is potentially useful for proteomics studies, and solid phase peptide synthesis techniques. The compound could be useful as an unusual amino acid analog to aid in the deconvolution of protein structure and function.

General DescriptionThe standard derivative for Fmoc SPPS of peptides containing Cys [1]. The Trt group is removed with 95% TFA containing 1-5% TIS. Ideally, this derivative should be introduced using the symmetrical anhydride or DIPCDI/HOBt activation [2,3] to minimize enantiomerization. If activation with uronium or phosphonium reagents, such as HBTU or PyBOP®, is to be employed, it is strongly recommended that collidine is used as the base [4], as this has been shown to significantly reduce loss of optical integrity during coupling.