S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-L-Ala) as an atom-efficient solubilising synthon for L-glutamine

Anne Beauchard, Elvis A Twum, Matthew D Lloyd, Michael D Threadgill

Research output: Contribution to journalArticle

Abstract

Glutamine (Gln) is often a difficult amino acid to incorporate during solution-phase peptide synthesis, owing to poor solubility and unwanted dehydrations as side-reactions. Current approaches to solving these problems are highly atom-inefficient. N(alpha)-Cbz-beta-cyanomethyl-L-Ala is readily accessible by dehydration of Cbz-L-Gln. beta-Cyanomethyl-L-Ala can be incorporated into short peptides easily by conventional methods. The nitrite is stable to the hydrogenolysis conditions used to remove Cbz and to acidic deprotection but is quantitatively hydrated to the gamma-carboxamide of L-Gln with hydrogen peroxide. Thus beta-cyanomethyl-L-Ala may represent a new, soluble, perfectly atom-efficient synthon for L-Gln.
LanguageEnglish
Pages5311-5314
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number41
DOIs
StatusPublished - 12 Oct 2011

Fingerprint

Glutamine
Atoms
Acids
Dehydration
Hydrogenolysis
Peptides
Nitrites
Solubility
Hydrogen Peroxide
Amino Acids

Cite this

S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-L-Ala) as an atom-efficient solubilising synthon for L-glutamine. / Beauchard, Anne; Twum, Elvis A; Lloyd, Matthew D; Threadgill, Michael D.

In: Tetrahedron Letters, Vol. 52, No. 41, 12.10.2011, p. 5311-5314.

Research output: Contribution to journalArticle

@article{bb028151738d4219a7a81ccd3b3f63c1,
title = "S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-L-Ala) as an atom-efficient solubilising synthon for L-glutamine",
abstract = "Glutamine (Gln) is often a difficult amino acid to incorporate during solution-phase peptide synthesis, owing to poor solubility and unwanted dehydrations as side-reactions. Current approaches to solving these problems are highly atom-inefficient. N(alpha)-Cbz-beta-cyanomethyl-L-Ala is readily accessible by dehydration of Cbz-L-Gln. beta-Cyanomethyl-L-Ala can be incorporated into short peptides easily by conventional methods. The nitrite is stable to the hydrogenolysis conditions used to remove Cbz and to acidic deprotection but is quantitatively hydrated to the gamma-carboxamide of L-Gln with hydrogen peroxide. Thus beta-cyanomethyl-L-Ala may represent a new, soluble, perfectly atom-efficient synthon for L-Gln.",
author = "Anne Beauchard and Twum, {Elvis A} and Lloyd, {Matthew D} and Threadgill, {Michael D}",
year = "2011",
month = "10",
day = "12",
doi = "10.1016/j.tetlet.2011.08.017",
language = "English",
volume = "52",
pages = "5311--5314",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "41",

}

TY - JOUR

T1 - S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-L-Ala) as an atom-efficient solubilising synthon for L-glutamine

AU - Beauchard,Anne

AU - Twum,Elvis A

AU - Lloyd,Matthew D

AU - Threadgill,Michael D

PY - 2011/10/12

Y1 - 2011/10/12

N2 - Glutamine (Gln) is often a difficult amino acid to incorporate during solution-phase peptide synthesis, owing to poor solubility and unwanted dehydrations as side-reactions. Current approaches to solving these problems are highly atom-inefficient. N(alpha)-Cbz-beta-cyanomethyl-L-Ala is readily accessible by dehydration of Cbz-L-Gln. beta-Cyanomethyl-L-Ala can be incorporated into short peptides easily by conventional methods. The nitrite is stable to the hydrogenolysis conditions used to remove Cbz and to acidic deprotection but is quantitatively hydrated to the gamma-carboxamide of L-Gln with hydrogen peroxide. Thus beta-cyanomethyl-L-Ala may represent a new, soluble, perfectly atom-efficient synthon for L-Gln.

AB - Glutamine (Gln) is often a difficult amino acid to incorporate during solution-phase peptide synthesis, owing to poor solubility and unwanted dehydrations as side-reactions. Current approaches to solving these problems are highly atom-inefficient. N(alpha)-Cbz-beta-cyanomethyl-L-Ala is readily accessible by dehydration of Cbz-L-Gln. beta-Cyanomethyl-L-Ala can be incorporated into short peptides easily by conventional methods. The nitrite is stable to the hydrogenolysis conditions used to remove Cbz and to acidic deprotection but is quantitatively hydrated to the gamma-carboxamide of L-Gln with hydrogen peroxide. Thus beta-cyanomethyl-L-Ala may represent a new, soluble, perfectly atom-efficient synthon for L-Gln.

UR - http://www.scopus.com/inward/record.url?scp=80052584430&partnerID=8YFLogxK

UR - http://dx.doi.org/10.1016/j.tetlet.2011.08.017

U2 - 10.1016/j.tetlet.2011.08.017

DO - 10.1016/j.tetlet.2011.08.017

M3 - Article

VL - 52

SP - 5311

EP - 5314

JO - Tetrahedron Letters

T2 - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 41

ER -