25840-83-9

Basic information

• Product Name: O-tritylserine
• Synonyms: H-Ser(Trt)-OH
• CAS NO: 25840-83-9
• Molecular Formula: C₂₂H₂₁NO₃
• Molecular Weight: 347.407
• Mol File: 25840-83-9.mol

Chemical Properties

• Boiling Point: 514.7°C at 760 mmHg
• Flash Point: 265.1°C
• Density: 1.209g/cm³
• Vapor Pressure: 2.04E-11mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: O-tritylserine(CAS DataBase Reference)
• NIST Chemistry Reference: O-tritylserine(25840-83-9)
• EPA Substance Registry System: O-tritylserine(25840-83-9)

Safety Data

• Hazardous Substances Data: 25840-83-9(Hazardous Substances Data)

Upstream product

• 111061-56-4 Fmoc-Ser(Trt)-OH 
• 76-84-6 triphenylmethyl alcohol 
• 56-45-1 L-serin 
• 76-83-5 trityl chloride 
• 16428-75-4 D,L-serine hydrochloride 

Downstream Products

• 252897-67-9 Boc-Ser(Trt)-OH 
• 111061-56-4 Fmoc-Ser(Trt)-OH 

Relevant articles and documents

Structure-activity relationship of S-trityl-L-cysteine analogues as inhibitors of the human mitotic kinesin Eg5

The human kinesin Eg5 is a potential drug target for cancer chemotherapy. Eg5 specific inhibitors cause cells to block in mitosis with a characteristic monoastral spindle phenotype. Prolonged metaphase block eventually leads to apoptotic cell death. S-trityl-L-cysteine (STLC) is a tight-binding inhibitor of Eg5 that prevents mitotic progression. It has proven antitumor activity as shown in the NCI 60 tumor cell line screen. It is of considerable interest to define the minimum chemical structure that is essential for Eg5 inhibition and to develop more potent STLC analogues. An initial structure-activity relationship study on a series of STLC analogues reveals the minimal skeleton necessary for Eg5 inhibition as well as indications of how to obtain more potent analogues. The most effective compounds investigated with substitutions at the para-position of one phenyl ring have an estimated Kiapp of 100 nM in vitro and induce mitotic arrest with an EC50 of 200 nM.

TRITYLATION REACTIONS BASED ON METALLIC CATALYSIS

The invention relates to a method for preparing tritylated compounds in which protic functional groups are protected with the triphenylmethyl group, method based on the homogeneous catalysis exercised by salts or metal complexes in organic solvents. The invention relates in particular to a method for the selective tritylation of some groups, obtained both directly and by selective detritylation, with methods based on metallic catalysis. The application to amino acids, typical substrates not suitable to be subjected as such to homogeneous tritylations in organic solvents, indicates the ability of the method to extend also to hydrophilic substrates. The method allows to obtain with high yield pertrityl amino acids, N-tritylamino acids or amino acids tritylated only in lateral chain, compounds which heretofore were either difficult to obtain in aqueous solvents or obtainable through indirect methods. All, in any case, are important intermediates in peptide synthesis.

Oxazole and thiazole combinatorial libraries

This invention provides a novel method for synthesizing an ensemble of peptides that allows for the generation of an unlimited number of antibiotic compounds. More specifically, the method comprises utilizes synthetic heterocyclic amino acids containing thaizole and/or oxazole as building blocks in a solid phase combinatorial synthesis to yield natural and unnatural antibiotic compounds.