Fmoc fluorenylmethyloxycarbonyl

Ac, acetyl AONs, antisense oligonucleotides B, boat Bn, benzyl Bz, benzoyl C, chair CD, circular dichroism CO, carbon monoxide ConA, concanavalin A DAST, diethylaminosulfur trifluoride DFT, density functional theory DMDO, dimethyldiox-irane DMT, dimethoxytriphenylmethyl DNA, deoxyribonucleic acid dsDNA, double-stranded DNA E, envelope Fmoc, fluorenylmethyloxycarbonyl GlcNAc, /V-acetylglucosamine ITC, isothermal titration calorimetry kcat, catalytic rate constant Aa, association constant K, inhibition constant KM, Michaelis constant LiSPh, lithium thiophenolate LPS, lipopolysaccharide pM, micromolar MMT,... 

Figure 10.18 Structure of phosphinoserine amino adds (Fmoc = fluorenylmethyloxycarbonyl).

FMOC = Fluorenylmethyloxycarbonyl HBTU = 2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate DIPEA = Diisopropylethylamine... 

The details of the solid-phase technique have been improved substantially over the years, but the fundamental idea remains the same. The most commonly used resins at present are either the Wang resin or the PAM (phenyl-acetamidomethyl) resin, and the most commonly used N-protecting group is the fluorenylmethyloxycarbonyl, or Fmoc group, rather than Boc. 

In the case of vancomycin [72], an original study was performed to obtain a well-defined stationary phase structure, since it was reasonably assumed that the antibiotic is randomly linked to the silica by one or both of its amino groups, one belonging to the disaccharide portion (primary), and the other one to the heptapeptide core (secondary). Thus, alternate fluorenylmethyloxycarbonyl (FMOC)-amino-protected derivatives were prepared and immobilized in a packed column, and then vancomycin was recovered by cleavage of the protecting groups. The two defined CSPs obtained, when compared with the CSP produced from native randomly linked vancomycin, showed lower retention and enantioselectivity, also if they still separated the same compounds. Thus, no advantages could be found to choose these phases as an alternative to the native vancomycin CSP. 

Other related reactions involve TV-fluorenylmethyloxycarbonyl (N-Fmoc) AAs and aliphatic aldehydes (83JOC77) or substituted /-butoxycarbonyl (N-Boc) Aas and 2,2-dimethyoxypropane (acetone dimethyl ketal) (84TL5855 87JOC2361 88TL2019), as well as A-(dimethylthio)methylene derivatives of an AA and aromatic aldehydes [89JCS(P1)1577]. 

It is called Fmoc (pronounced elf-mock ), for fluorenylmethyloxycarbonyl, and has a susceptibility inverse to that of f-Boc. It cannot be lost by substitution in the manner of Cbz or f-Boc because neither S l nor S>j2 mechanisms can operate at the ringed carbon atom it is both primary and hindered. 

Standard amino acid protecting groups that were used routinely in BOC-peptide synthesis. For Lys the -nitrogen has the potential to cyclize. We sometimes protect this with the fluorenylmethyloxycarbonyl (FMOC) protecting group. 

The definitive paper on the 9-fluorenylmethyloxycarbonyl group (FMOC) for protection of an amino group has been published. ... 

Abbreviations Standard abbreviations as recommended by IUPAC-1UB Commission are used in this review (1). Other abbreviations include Acm, acetamidomethyl Bn, benzyl Boc t-butyloxycarbonyl Bom, benzyloxymethyl BHA, benzhydrylamine Cbz, benzyloxycarbonyl cHx, cyclohexyl DCC, N,N-dicyclohexylcarbodiimide DCM, dichloromethane Die, N,N-diisopropylcarbodiimide DMF, N,N-dimethylformamide DMSO, dimethyl sulphoxide For, formyl Fmoc, 9-fluorenylmethyloxycarbonyl HMP, 4-hydroxymethylphenoxyacetyl HOAt,... 

Treatment of cycloserine with Fmoc-Cl or Fmoc-OSu in the presence of pyridine afforded a mixture of endo- and exocyclic N-acylated products (Fmoc = 9-fluorenylmethyloxycarbonyl). Selective protection of the primary amine was achieved on multigram scale and in high yield by in situ formation of the bis-silylated derivative with T,0-bis(trimethylsilyl)acetamide (BSA) followed by acylation (Scheme 76) <1998T15879>. 

PAL resin, fluorenylmethyloxycarbonyl (Fmoc) and butyloxycarbonyl (Boc) amino acids with standard side chain protection and Boc-Tyr(tBu)-OH were from Advanced ChemTech (Louisville, KY, USA). FmocLys(Dde ) was from BioChem (San Diego, CA, USA). Beta-endorphin and anti-P-endorphin (3-E7) were from Boehringer Mannheim. The photocleavable biotinylated linker was prepared according to the literature procedure (4). 

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