Convergent and facile synthesis of hybrid sulfonophosphonodipeptides

Biyun Sun; Jiaxi Xu

doi:10.1055/s-0034-1380267

Convergent and facile synthesis of hybrid sulfonophosphonodipeptides

Biyun Sun, Jiaxi Xu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

A convergent and facile method has been developed for the preparation of hybrid sulfonophosphonodipeptides composed of 2-aminoalkanesulfonic acid and 1-aminoalkylphosphonic acid residues. A series of hybrid sulfonophosphonodipeptides were synthesized in satisfactory yields via the Mannich-type reaction of 2-(Cbz-amino)alkanesulfonamides, aldehydes, and phosphorus trichloride, followed by sequential hydrolysis. The reaction mechanism was proposed and verified by NMR tracing experiments.

Original language	English
Article number	ss-2014-h0782-op
Pages (from-to)	1479-1487
Number of pages	9
Journal	Synthesis (Germany)
Volume	47
Issue number	10
DOIs	https://doi.org/10.1055/s-0034-1380267
Publication status	Published - 1 May 2015
Externally published	Yes

Keywords

hybrid peptide
hydrolysis
Mannich reaction
phosphonopeptide
sulfonamide
sulfonopeptide

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10.1055/s-0034-1380267

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title = "Convergent and facile synthesis of hybrid sulfonophosphonodipeptides",

abstract = "A convergent and facile method has been developed for the preparation of hybrid sulfonophosphonodipeptides composed of 2-aminoalkanesulfonic acid and 1-aminoalkylphosphonic acid residues. A series of hybrid sulfonophosphonodipeptides were synthesized in satisfactory yields via the Mannich-type reaction of 2-(Cbz-amino)alkanesulfonamides, aldehydes, and phosphorus trichloride, followed by sequential hydrolysis. The reaction mechanism was proposed and verified by NMR tracing experiments.",

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author = "Biyun Sun and Jiaxi Xu",

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T1 - Convergent and facile synthesis of hybrid sulfonophosphonodipeptides

AU - Sun, Biyun

AU - Xu, Jiaxi

PY - 2015/5/1

Y1 - 2015/5/1

N2 - A convergent and facile method has been developed for the preparation of hybrid sulfonophosphonodipeptides composed of 2-aminoalkanesulfonic acid and 1-aminoalkylphosphonic acid residues. A series of hybrid sulfonophosphonodipeptides were synthesized in satisfactory yields via the Mannich-type reaction of 2-(Cbz-amino)alkanesulfonamides, aldehydes, and phosphorus trichloride, followed by sequential hydrolysis. The reaction mechanism was proposed and verified by NMR tracing experiments.

AB - A convergent and facile method has been developed for the preparation of hybrid sulfonophosphonodipeptides composed of 2-aminoalkanesulfonic acid and 1-aminoalkylphosphonic acid residues. A series of hybrid sulfonophosphonodipeptides were synthesized in satisfactory yields via the Mannich-type reaction of 2-(Cbz-amino)alkanesulfonamides, aldehydes, and phosphorus trichloride, followed by sequential hydrolysis. The reaction mechanism was proposed and verified by NMR tracing experiments.

KW - hybrid peptide

KW - hydrolysis

KW - Mannich reaction

KW - phosphonopeptide

KW - sulfonamide

KW - sulfonopeptide

UR - https://www.scopus.com/pages/publications/84933044844

U2 - 10.1055/s-0034-1380267

DO - 10.1055/s-0034-1380267

M3 - Article

AN - SCOPUS:84933044844

SN - 0039-7881

VL - 47

SP - 1479

EP - 1487

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 10

M1 - ss-2014-h0782-op

ER -

Convergent and facile synthesis of hybrid sulfonophosphonodipeptides

Abstract

Keywords

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