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Conformations of the pyranoid sugars.II. Infrared absorption spectra of some aldopyranosides

1960; The National Institute of Standards and Technology; Volume: 64A; Issue: 3 Linguagem: Inglês

10.6028/jres.064a.025

2376-5704

R. Stuart Tipson, Horace S. Isbell,

Microbial Metabolites in Food Biotechnology

The co nform ation s of t wen ty-four aldopyranos id es h a ve been st udi ed by a nal ys is of t he ij• infra red absorpt ion spectra.The m ost stable co nform ations of t wel ve of t he glycos id es h ad p reviollsly been assig ned by R ee ves from a st ud y of t heir in stabilit y fa ctors; these conformations wer e aSS lim ed t o apply t o t he cr ystalline state, for whi ch t h e s pec tra h a d bee n recorded .The compounds were classifi ed in to (a) co nfi gurationally an d (b) structurally r elated .groups, a nd.t he spectra were in tercompared .The an alys is r evealed grou ps of absor pt lOll ba nds whi ch sh owed a co ncerted shift on chan ge of a nomeri c di spos it ion.Wi t h t hese groups of absorp tion bands t hus ident ifi ed , in tercompa ri son wit ll n ine of t he rem ain ing sp ectra afford ed evidence t hat t he a nomer ic group (1) is ftx ial in m ethyl D-glycero-a-I,-gluco-heptopyra no ide, m ethy l D-gl ycero-a-L-manno-heptopyran osid e, and methyl D-glycero-a-D-gulo-hep to pyra nosid e; (2) i equ ato ri al in m etllyI6-deoxy-j3-L-mannopyr anosid e, meth y I D-glyce1•o-j3-D-gu lo-hep to p yr an osid e, a nd cyclo hexy I D-glyceTo-j3-D-gulo-heptopy ra nos id e; a nd (3) eit her i quasi or occ urs as differen t (or mi xed) axial a nd eq u atori al forms in methy l a-D-Iyxopranoside, met hyl j3-D-lyxopranoside, a nd (possibly) a-D-m ethylgulopyra,noside.Tlu•ee of t he glyeosides were ava il a bl e as t heir cr ystallin e complexes with calciu m chl oride.The spectra of t he e complexes were also exam in ed, a nd t he efTect of co-c rystalli zat io n with ca lciu m chlorid e is pointed out .I Figures in bra ckets indicate the li terature references at the end of t his pa per.' l' he r efere nces for table 1 are give n a t the end of Lhe table.'The method of compa ri so n is being ap plied to other gro ups of stru cturall y related pyranoid suga r derivati ves.3 Code numbers a rc assigned according to a previously p ublished ciass ificalionl system [51, for use with pUJ1 ched•card techniques .