S-Fluorenylmethyl protection of the cysteine side chain upon N^α-Fmoc deprotection

Abstract

SummaryDeprotection of an N α-Fmoc-protected glycocysteine derivative 7 with an excess of morpholine unexpectedly led to the fluorenylmethyl-protected thioether 8 in high yield. The suggested mechanism for this reaction comprises the addition of the cysteine thiolate on the exocyclic double bond of dibenzofulvene, which is formed during Fmoc deprotection. The influence of base concentration on this transprotection reaction was studied.

New methodology for automated SPOT synthesis of peptides on cellulose using 1,3,5‐triazine derivatives as linkers and as coupling reagents

“…As previously, the attachment of the second Fmoc protected amino acid residue was monitored by spectrometric determination of dibenzofulvene, which formed after deprotection of the Fmoc group with 25% piperidine in DMF . The loading was diversified and depended on the structure of the acylated residue.…”

Anti-cancerous/Anti-bacterial Activities of Allicin Generated In situ from Diastereo Pure Alliins by Alliinase

“…Compound 6 was synthesized following a procedure with modifications [30][31][32][33]. Alliin (3.3 mg, 1 equiv) was dissolved in 660 µL of water and NaHCO 3 (6.2 mg, 4 equiv), Na 2 CO 3 (3.9 mg, 2 equiv), and 50 µL of 1,4-dioxane was added in sequence.…”