Fmoc-S-Trityl-L-penicillamine Chemical Properties

Boiling point:

768.8±60.0 °C(Predicted)

alpha 

33 º (c=1 in methanol)

Density 

1.242±0.06 g/cm3(Predicted)

storage temp. 

Store at -15°C to -25°C.

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

3.70±0.10(Predicted)

color 

White to off-white

optical activity

[α]/D +33±2°, c = 1 in methanol

Major Application

peptide synthesis

InChI

InChI=1S/C39H35NO4S/c1-38(2,45-39(27-16-6-3-7-17-27,28-18-8-4-9-19-28)29-20-10-5-11-21-29)35(36(41)42)40-37(43)44-26-34-32-24-14-12-22-30(32)31-23-13-15-25-33(31)34/h3-25,34-35H,26H2,1-2H3,(H,40,43)(H,41,42)/t35-/m1/s1

InChIKey

XSGMGAINOILNJR-PGUFJCEWSA-N

SMILES

C(O)(=O)[C@H](C(SC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C)C)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O

CAS DataBase Reference

201531-88-6(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

2930 90 16

HazardClass 

IRRITANT

Storage Class

11 - Combustible Solids

Fmoc-S-Trityl-L-penicillamine Usage And Synthesis

Description

Fmoc-S-trityl-L-penicillamine is a coordination compound that contains a thiolate and amide group. It has been used as a model system for studying the interaction between proteins and metal ions, with the cyclic structure mimicking the active site of enzymes. The coordination of Fmoc-S-trityl-L-penicillamine to proteins is affected by trypsin, an enzyme that cleaves peptides at carboxyl side chains. Trypsin can also lead to dehydration of Fmoc-S-trityl-L-penicillamine, forming an eliminations product. This compound also reacts with lysine residues in proteins, resulting in an alkene byproduct that can be removed by hydrogenation.

Chemical Properties

White to off-white powder

Uses

Fmoc-s-trityl-l-penicillamine is a new peptidomimetic furin inhibitors with potent anti-infectious activity.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

11mmol, 1.1eq Fmoc-Cl was added dropwise to a solution of dichloromethane containing 10mmol, 1eq of S-trityl-L-cysteine and 30ml of sodium bicarbonate containing 13mmol, 1.3eq of sodium bicarbonate under an ice-salt bath, and the reaction solution was brought up to room temperature after dropwise addition. The reaction was finished for 12h. The reaction solution was filtered and the filter cake plus washed with dichloromethane and the organic phase was combined. The organic phase was washed once with 20 ml of dilute sodium bicarbonate solution, 20 ml, 0.5 M dilute hydrochloric acid and 30 ml of saturated saline, then the organic phase was dried with anhydrous sodium sulfate for 2h, filtered, spin-dried solvent, the target product Fmoc-S-trityl-L-penicillamine was obtained.

Fmoc-S-Trityl-L-penicillamine(201531-88-6)Related Product Information

• p-Toluic acid
• 1,1'-Carbonyldiimidazole
• Triphenylmethyl Chloride
• Fmoc-N'-methyltrityl-L-lysine
• Trityl candesartan cilexetil
• 9-Fluorenylmethyl chloroformate
• L-Penicillamine
• Fmoc-8-amino-3,6-dioxaoctanoic acid
• Dimethyl fumarate
• FMOC-S-trityl-L-cysteine
• FMOC-4-[2-(BOC-AMINO)ETHOXY]-L-PHENYLALANINE
• Fmoc-Phe(4-CF2H)-OH
• L-Phenylalanine, 3-[(1,1-dimethylethoxy)carbonyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-
• Fmoc-OSu
• D-Penicillamine
• FMOC-THR(TBU)-OL
• FMOC-ASU-OH
• Fmoc-phe(2-Ae-Z)-OH