13C nuclear magnetic resonance data of bile acid derivatives

Dias, Jerry Ray; Gao, Hongwu; Kolehmainen, Erkki

doi:10.1016/s1386-1425(99)00135-3

Cited by 34 publications

(1 citation statement)

References 18 publications

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“…Total assignations of the 13 C-NMR spectra of steroids have been done over 20 years and a great number of the 13 C-NMR shift data of bile acids and their derivatives have been published [58][59][60][61][62][143][144][145][146][147][148][149]. Dias et al have identified a diagnostic 13 C-NMR γ-oxygen shielding effect which in addition to the deshielding effect on the carbon bearing the electronegative oxygen identifies whether this substituent is oriented axial or equatorial [149].…”

Section: Nmr Spectroscopymentioning

confidence: 99%

Bile Acids as Building Blocks of Supramolecular Hosts

Tamminen

Kolehmainen

2001

ChemInform

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Section: Nmr Spectroscopymentioning

confidence: 99%

Bile Acids as Building Blocks of Supramolecular Hosts

Tamminen

Kolehmainen

2001

ChemInform

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Short Synthesis of Orthogonally Protected 3α,12α‐Diamino‐5β‐cholan‐24‐oic Acid, a Dipodal Steroid Scaffold for Combinatorial Chemistry

Verzele

Madder

2007

Eur J Org Chem

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A short, practical, multigram-scale synthesis of C3α-NHAlloc, C12α-NHBoc-diamino-5β-cholan-24-oic acid 2 was developed, applying a new, straightforward synthetic strategy. Key features are the conservation of the carboxyl moiety at C24 during oxime reduction, the late differentiation between the C3 and C12 amino groups and the gradual separa- IntroductionThe steroid core has proven to be a versatile building block for the design of frameworks capable of ionic [1] and molecular recognition, [2] the preparation of antimicrobial agents [3] and novel amphiphiles. [4] Bile acid based systems can be further important in the understanding of the functioning of natural systems. Moreover, steroids have found extensive application as scaffold for the assembly of combinatorial libraries.[5] Therefore research on bile acids, their derivatives and potential applications is actively pursued. [6] In order to attain these goals and to broaden the plethora of possible applications, a fast, easy and efficient access to these steroid building blocks is needed. Our earlier efforts in the area concerned the construction of heterodipodal peptidosteroid libraries of potential serine protease mimics and were based on the use of the C3α-NHAlloc-, C7α-OAc-, C12α-NHBoc-protected diamino steroid scaffold 1 (Figure 1). The synthesis of suitable quantities of scaffold starting material was a difficult and time-consuming task.[7] Starting [a]

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Multinuclear magnetic resonance, electrospray ionization time‐of‐flight mass spectral and molecular modelling characterization of lithocholic acid amide esters with various nitrogen heterocycles

Virtanen

Tamminen

Haapala

et al. 2003

Magnetic Reson in Chemistry

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1 H, 13 C and 15 N NMR and electrospray ionization time-of-flight mass spectrometric characterizations of five lithocholate esters of piperazine diamides are described. Two of them are cholaphane-type cyclic structures esterified with 2,2 -bipyridine-4,4 -and pyridine-2,6-dicarboxylic acid and the other three esters are open structures comprising two or four lithocholyl residues. The conformational preferences of the dimeric congeners were examined by using molecular modelling and variable-temperature 1 H NMR techniques.

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13C nuclear magnetic resonance data of bile acid derivatives

Cited by 34 publications

References 18 publications

Bile Acids as Building Blocks of Supramolecular Hosts

Bile Acids as Building Blocks of Supramolecular Hosts

Short Synthesis of Orthogonally Protected 3α,12α‐Diamino‐5β‐cholan‐24‐oic Acid, a Dipodal Steroid Scaffold for Combinatorial Chemistry

Multinuclear magnetic resonance, electrospray ionization time‐of‐flight mass spectral and molecular modelling characterization of lithocholic acid amide esters with various nitrogen heterocycles

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