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Soluble polymer supports for liquid-phase synthesis

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Polymer Synthesis/Polymer Engineering

Part of the book series: Advances in Polymer Science ((POLYMER,volume 121))

Abstract

This review presents a survey on functional soluble polymers in view of their use as supports for liquid-phase synthesis. The general aspects of synthesis in homogeneous media as well as analytical and separation problems are discussed, focussing on the role of the polymer in the synthetic cycle and the problems associated with polymer-supported reactions. A survey of polymeric carriers in respect of their functional groups and backbones is provided with an emphasis on poly(oxyethylene), polystyrene, and poly(vinyl alcohol) supports. Combined methods using solid and soluble supports are also highlighted. The polymeric carriers are discussed and evaluated for their use in peptide and nucleotide synthesis. Finally an outlook into future developments is attempted.

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Abbreviations

A:

Amino acid or Adenosine

Ac:

Acetyl

AIBN:

2,2′-Azobisisobutyronitrile

Ala:

Alanine

Arg:

Arginine

Asn:

Asparagine

Boc:

tert-Butyloxycarbonyl

bz:

Benzoyl

Bzl:

Benzyl

Cys:

Cysteine

d:

2′-Deoxyribonucleoside

DCC:

N,N′-Dicyclohexylcarbodiimide

DCM:

Dichloromethane

DMF:

N,N′-Dimethylformamide

dT:

Deoxythymidine

Glu:

Glutamic acid

Gly:

Glycine

HAc:

Acetic acid

Ile:

Isoleucine

Leu:

Leucine

\(\bar M\) :

Average molecular mass

Met:

Methionine

NMM:

N-Methylmorpholine

Np:

Nitrophenyl

Nuc:

Nucleotide

P:

Polymer

p:

Phosphoric acid residue

pdT:

2′-Deoxythymidine monophosphate

PEG:

Poly(ethylene glycol); αω-Dihydroxy poly(oxyethylene)

Phe:

Phenylalanine

POE:

Poly(oxyethylene); mono- or bifunctional

Pro:

Proline

PS:

Polystyrene

PSC:

Polystyrene, crosslinked

PVA:

Poly(vinyl alcohol)

Ser:

Serine

T:

Thymidine

Th:

Thymine

THF:

Tetrahydrofuran

TPS:

Triisopropyl benzenesulfonyl chloride

Tos:

Tosyl; 4-Methylbenzenesulfonyl

Trit:

Trityl

U:

Uracil

Val:

Valine

X:

Functional group

Y:

Protecting group

Z:

Benzyloxycarbonyl

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  1. Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, D-72076, Tübingen, Germany

    K. E. Geckeler

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Geckeler, K.E. (1995). Soluble polymer supports for liquid-phase synthesis. In: Polymer Synthesis/Polymer Engineering. Advances in Polymer Science, vol 121. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0018578

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  • DOI: https://doi.org/10.1007/BFb0018578

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