Scalable Synthesis of L-allo-Enduracididine: The Unusual Amino Acid Present in Teixobactin

Synlett ◽

10.1055/a-1528-0625 ◽

2021 ◽

Author(s):

Srivari Chandrashekar ◽

Namdeo Gangathade ◽

Kiranmai Nayani ◽

Hemalatha Bukya ◽

Prathama S Mainkar

Keyword(s):

Amino Acid ◽

Synthetic Route ◽

Asymmetric Dihydroxylation ◽

Scalable Synthesis ◽

Unusual Amino Acid ◽

Synthetic Transformations

A scalable synthesis of L-allo-enduracididine is achieved from commercially available (S)-glycidol in ten linear steps involving well established synthetic transformations. The synthetic route is flexible and can be used to synthesize all four diastereomers, by changing the stereochemistry of glycidol and Sharpless asymmetric dihydroxylation reagent.

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Scalable synthesis of the unusual amino acid segment (ADMOA unit) of marine anti-inflammatory peptide: solomonamide A

Organic & Biomolecular Chemistry ◽

10.1039/c5ob00481k ◽

2015 ◽

Vol 13 (22) ◽

pp. 6242-6248 ◽

Cited By ~ 8

Author(s):

Nerella Kavitha ◽

Srivari Chandrasekhar

Keyword(s):

Amino Acid ◽

New Approach ◽

Anti Inflammatory ◽

Scalable Synthesis ◽

Amino Acid Segment ◽

Unusual Amino Acid

A new approach has been developed for the synthesis of the unusual amino acid segment (ADMOA unit) of solomonamide A starting from d-glucose.

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Synthetic study on dolastatin 16: concise and scalable synthesis of two unusual amino acid units

Tetrahedron Letters ◽

10.1016/j.tetlet.2014.11.054 ◽

2015 ◽

Vol 56 (1) ◽

pp. 168-171 ◽

Cited By ~ 6

Author(s):

Taiki Umezawa ◽

Akinori Sato ◽

Yasuto Ameda ◽

Loida O. Casalme ◽

Fuyuhiko Matsuda

Keyword(s):

Amino Acid ◽

Scalable Synthesis ◽

Unusual Amino Acid

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ChemInform Abstract: An Enantiospecific Synthesis of L(-)- and D(+)-6-Chloro-5- hydroxytryptophan: An Unusual Amino Acid Residue from the Cyclic Hexapeptide Keramamide A.

ChemInform ◽

10.1002/chin.199604232 ◽

2010 ◽

Vol 27 (4) ◽

pp. no-no

Author(s):

P. ZHANG ◽

R. LIU ◽

J. M. COOK

Keyword(s):

Amino Acid ◽

Amino Acid Residue ◽

Cyclic Hexapeptide ◽

Enantiospecific Synthesis ◽

Unusual Amino Acid

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Convenient Synthetic Route to an Enantiomerically Pure FMOC α-Amino Acid

The Journal of Organic Chemistry ◽

10.1021/jo801781v ◽

2008 ◽

Vol 73 (23) ◽

pp. 9334-9339 ◽

Cited By ~ 10

Author(s):

Douglass F. Taber ◽

James F. Berry ◽

Timothy J. Martin

Keyword(s):

Amino Acid ◽

Synthetic Route ◽

Enantiomerically Pure

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An unusual amino acid sequence of an AL-protein, AL-109, derived from a kappa I chain

Amyloid ◽

10.3109/13506120108993825 ◽

2001 ◽

Vol 8 (4) ◽

pp. 274-276 ◽

Cited By ~ 1

Author(s):

Shucking Wang ◽

Knut Sletten ◽

Per Westermark

Keyword(s):

Amino Acid ◽

Amino Acid Sequence ◽

Unusual Amino Acid

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Size-tunable and scalable synthesis of uniform copper nanocrystals

RSC Advances ◽

10.1039/c4ra09756d ◽

2015 ◽

Vol 5 (4) ◽

pp. 2756-2761 ◽

Cited By ~ 6

Author(s):

Hwansu Sim ◽

Jihwan Lee ◽

Taekyung Yu ◽

Kyungpil Kim ◽

Seong Jun Lee ◽

...

Keyword(s):

Ethylene Glycol ◽

Synthetic Method ◽

Synthetic Route ◽

Scalable Synthesis

A facile and scalable synthetic route to uniform Cu nanocrystals with tunable sizes in the range of 20–100 nm based on an ethylene glycol-assisted synthetic method was developed.

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Neisseria pili proteins: amino-terminal amino acid sequences and identification of an unusual amino acid

Biochemistry ◽

10.1021/bi00596a010 ◽

1978 ◽

Vol 17 (3) ◽

pp. 442-445 ◽

Cited By ~ 91

Author(s):

Mark A. Hermodson ◽

Kirk C. S. Chen ◽

Thomas M. Buchanan

Keyword(s):

Amino Acid ◽

Amino Acid Sequences ◽

Terminal Amino Acid ◽

Amino Terminal ◽

Terminal Amino ◽

Unusual Amino Acid

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Scalable Synthesis of High-Purity (R, R)-Dexmethylphenidate Free Base

International Journal of Chemistry ◽

10.5539/ijc.v8n4p28 ◽

2016 ◽

Vol 8 (4) ◽

pp. 28 ◽

Cited By ~ 1

Author(s):

Guan Wang ◽

Dongsheng Chen ◽

Yuanyuan Sun ◽

Qing Cao ◽

Bonan Li ◽

...

Keyword(s):

Amino Acid ◽

High Purity ◽

Industrial Production ◽

Acid Ester ◽

Substitution Reaction ◽

Practical Method ◽

Amino Acid Ester ◽

Free Base ◽

Hydrochloride Salt ◽

Scalable Synthesis

<p>A practical method for the preparation of high-purity (<em>R, R</em>)-dexmethylphenidate free base was developed. The method involves a substitution reaction of 2-chloropyridine and phenylacetonitrile via hydrolysis followed by hydrogenation, configuration inversion, chiral resolution, methyl esterification, and salification to give high-purity dexmethylphenidate hydrochloride. The hydrochloride salt was then neutralized by powder sodium hydroxide overnight to give dexmethylphenidate free base with over 99% purity. This method can be used for the industrial production of the dexmethylphenidate patch API, which could also be further applied for the preparation of other types of amino acid ester free bases.</p>

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