PMID- 2979735
OWN - NLM
STAT- MEDLINE
DCOM- 19920309
LR  - 20190919
IS  - 0893-228X (Print)
IS  - 0893-228X (Linking)
VI  - 1
IP  - 4
DP  - 1988 Jul-Aug
TI  - N-glycolylhydroxamic acids: an improved synthetic method and the in situ 
      generation and intramolecular rearrangement of 
      N-acetoxy-N-glycolyl-2-aminofluorene.
PG  - 222-7
AB  - A new and improved method for the synthesis of glycolylhydroxamic acids is 
      described. The two-step method involves acylation of arylhydroxylamines with 
      acetoxyacetyl chloride, followed by saponification of the ester bond to give the 
      desired products. The conversion of hydroxamic acids to their thallous salts 
      followed by subsequent acetylation with acetyl chloride to give N-acyloxy esters 
      is described. During the course of this investigation, it was observed that the 
      N-acetoxy ester of an N-glycolylhydroxamic acid was highly unstable and underwent 
      a novel O----O acyl migration. This facile rearrangement reaction was studied for 
      the case of N-acetoxy-N-glycolyl-2-aminofluorene (N-OAc-GAF), which gave 
      N-hydroxy-N-(acetoxyacetyl)-2-aminofluorene (N-OH-AcAAF) as the sole product of 
      this rearrangement. HPLC was used to investigate this reaction and included the 
      assignment of an HPLC peak to be due to N-OAc-GAF. A competition study employed 
      the amide N-glycolyl-2-aminofluorene (GAF) and demonstrated the absence of 
      intermolecular transfer of the N,O-acyl (acetyl) group of N-OAc-GAF. The 
      mechanism for the probable intramolecular rearrangement reaction is presented, 
      along with a consideration of the possible significance it might have for the 
      toxicity of glycolylhydroxamic acids.
FAU - Corbett, M D
AU  - Corbett MD
AD  - Food Science & Human Nutrition Department, University of Florida, Gainesville 
      32611.
FAU - Corbett, B R
AU  - Corbett BR
LA  - eng
GR  - ES 03631/ES/NIEHS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - United States
TA  - Chem Res Toxicol
JT  - Chemical research in toxicology
JID - 8807448
RN  - 0 (Hydroxamic Acids)
RN  - 0 (Indicators and Reagents)
RN  - 115227-95-7 (N-acetoxy-N-glycolyl-2-aminofluorene)
RN  - 53-95-2 (Hydroxyacetylaminofluorene)
RN  - EC 2.2.1.1 (Transketolase)
SB  - IM
MH  - Hydroxamic Acids/*chemical synthesis
MH  - Hydroxyacetylaminofluorene/*analogs & derivatives/chemical synthesis/chemistry
MH  - Indicators and Reagents
MH  - Molecular Structure
MH  - Transketolase/metabolism
EDAT- 1988/07/01 00:00
MHDA- 1988/07/01 00:01
CRDT- 1988/07/01 00:00
PHST- 1988/07/01 00:00 [pubmed]
PHST- 1988/07/01 00:01 [medline]
PHST- 1988/07/01 00:00 [entrez]
AID - 10.1021/tx00004a006 [doi]
PST - ppublish
SO  - Chem Res Toxicol. 1988 Jul-Aug;1(4):222-7. doi: 10.1021/tx00004a006.