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Chemical structure of Fmoc-Cys(4-methoxytrityl)-OH

GA21557

Fmoc-Cys(4-methoxytrityl)-OH

Also known as (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(4-methoxyphenyl)-diphenylmethyl]sulfanylpropanoic acid

4-Methoxytrityl (Mmt) is a very acid-sensitive cysteine protecting group that can selectively be removed by 0·5-1·0% TFA in the presence of scavengers, e·g· TES· Protecting groups of the t-butyl type and S-Trt are left intact under these conditions· Cleavage and cyclization can be achieved concomitantly by adding iodine· It can be used in the solid-phase synthesis of cysteine-containing peptides, and further to selectively deprotect a thiol function in order to introduce a labeling group· Rijkers et al· employed p-methoxytrityl protection for obtaining S-palmitoylated peptides on-resin· The high acid lability of Cys(Mmt) was exploited by Roberts et al· to obtain a library of thioether-linked cyclic peptides· Arendt et al· employed Cys(Mmt) for the synthesis of peptides containing cysteic acid by selective deblocking and oxidation of the thiol moiety with performic acid· Mmt is fully stable to HOBt

ChemicalCAS177582-21-7MW615.76FormulaC38H33NO5S
CAS number
177582-21-7
Molecular weight
615.76
Formula
C38H33NO5S
Solubility
Soluble in DMSO
InChIKey
LOBUWFUSGOYXQX-DHUJRADRSA-N
Catalogue number
GA21557
Brand
GLPBIO
Computed properties PubChem CID 10995693 · XLogP 8 · TPSA 110 Ų · H-bond donors 2
XLogP
8
TPSA
110 Ų
H-bond donors
2
H-bond acceptors
6
Rotatable bonds
12
Heavy atoms
45

SMILES COC1=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

Computed descriptors from PubChem (CID 10995693), public domain. Identity cross-checked against the supplier's molecular formula and weight — verify before use.

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