Catalog Number
ACM150629677
Product Name
Fmoc-Lys(Dde)-OH
Description
Quasi-orthogonally-protected Lys derivative for Fmoc SPPS. The Fmoc group can be removed selectively by treatment with piperidine; the Dde group is cleaved with 2% hydrazine in DMF. When removing Dde in the presence of allyl based protecting groups, allyl alcohol should be included in the deprotection solution to prevent reduction of the allyl group. Lys(Dde) has been employed in the following applications: synthesis of branched peptides and di-epitopic peptides ; preparation of MAP core molecules and lipo-MAPs; construction of cyclic peptides , TASP molecules , templates for combinatorial chemistry and synthetic proteins ; preparation of peptides modified at the lysine side-chain.It has been reported that Dde can migrate from the side-chain of Lys to the unprotected side-chain of another Lys residue , and from the β-amino group to the α-amino group of Dpr. In the former instance, this problem can be overcome by using Fmoc-Lys(ivDde)-OH or using DBU/DMF (2:98) for Fmoc group removal.Full orthogonality of Dde with Fmoc has recently been demonstrated when hydroxylamine is used for Dde removal.
Synonyms
Fmoc-Lys(Dde)-OH, N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-lysine
Molecular Formula
C31H36N2O6
InChI
1S/C31H36N2O6/c1-19(28-26(34)16-31(2,3)17-27(28)35)32-15-9-8-14-25(29(36)37)33-30(38)39-18-24-22-12-6-4-10-20(22)21-11-5-7-13-23(21)24/h4-7,10-13,24-25,34H,8-9,14-18H2,1-3H3,(H,33,38)(H,36,37)/t25-/m0/s1
InChI Key
AOHSSQNORWQENF-VWLOTQADSA-N
Melting Point
80 ℃(decomposes)
Application
Peptide synthesis.
Assay
≥90.0% (acidimetric)
≥97.0% (HPLC)
≥98% (TLC)
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis
Storage Temperature
15-25℃
Type
Unlabeled Standard Amino Acids, Lysine (Lys)
Download
