How SH of cysteine is protected in peptide synthesis?
Cysteinyl Protection. For routine synthesis of cysteinyl peptide containing free thiol groups, the trityl group is particularly recommended, as it is labile to TFA (trifluoroacetic acid) and is therefore removed during the normal cleavage procedure.
What are protecting groups in organic chemistry?
A protecting group (PG) is a molecular framework that is introduced onto a specific functional group (FG) in a poly-functional molecule to block its reactivity under reaction conditions needed to make modifications elsewhere in the molecule.
What is Tipso in chemistry?
Triisopropyl silane (TIPS) is an organosilicon compound with the formula (i-Pr)3SiH (i-Pr = isopropyl). This colorless liquid is used as a scavenger in peptide synthesis. TIPS is able to scavenge carbocations formed in the deprotection of a peptide as it can act as a hydride donor in acidic conditions.
What is the use of FMOC protecting group in organic synthesis?
Fmoc protection has found significant use in solid phase peptide synthesis (SPPS), because its removal with piperidine solution does not disturb the acid labile linker between the peptide and the resin. A typical SPPS Fmoc deprotection is performed with a 20% solution of piperidine in N,N-dimethylformamide.
How do you Deprotect FMOC?
The Fmoc group is, in general, rapidly removed by primary (i.e., cyclohexylamine, ethanolamine) and some secondary (i.e., piperidine, piperazine) amines, and slowly removed by tertiary (i.e., triethylamine [Et3N], N, N-diisopropylethylamine [DIEA]) amines.
How does triisopropylsilane remove cysteine-S-Protecting groups?
Reduction of cysteine-S-protecting groups by triisopropylsilane. Triisopropylsilane (TIS), a hindered hydrosilane, has long been utilized as a cation scavenger for the removal of amino acid protecting groups during peptide synthesis. However, its ability to actively remove S-protecting groups by serving as a reductant has largely been
Is triisopropylsilane a cation scavenger or reductant?
Triisopropylsilane (TIS), a hindered hydrosilane, has long been utilized as a cation scavenger for the removal of amino acid protecting groups during peptide synthesis. However, its ability to actively remove S-protecting groups by serving as a reductant has largely been mischaracterized by the peptide community.
Why is triisopropylsilane used in the preparation of tryptophan-containing peptides?
The use of triisopropylsilane minimizes the risk of reduction of the indole nucleus in tryptophan-containing peptides: Tetrahedron Lett., 30, 2739 (1989). See Appendix 6.
What is the difference between ethyl and isopropyl groups?
The bulky isopropyl groups (vs. ethyl) allow for more selective reductions, e.g., beta-selective reduction of anomeric C-phenyl ketals, but do not diminish their activity (e.g. in the copper triflate catalyzed reductive etherification of trimethylsilyl ethers).