316172-74-4

Basic information

• Product Name: L-Aspartic acid, 3-methoxy-, (3S)- (9CI)
• Synonyms: L-Aspartic acid, 3-methoxy-, (3S)- (9CI)
• CAS NO: 316172-74-4
• Molecular Formula: C₅H₉NO₅
• Molecular Weight: 163.12866
• Product Categories: GLYCINESCAFFOLD
• Mol File: 316172-74-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Aspartic acid, 3-methoxy-, (3S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: L-Aspartic acid, 3-methoxy-, (3S)- (9CI)(316172-74-4)
• EPA Substance Registry System: L-Aspartic acid, 3-methoxy-, (3S)- (9CI)(316172-74-4)

Safety Data

• Hazardous Substances Data: 316172-74-4(Hazardous Substances Data)

Upstream product

• 700816-76-8 (2S,3R)-β-methoxytyrosine 

Relevant articles and documents

Total Synthesis and Structural Establishment/Revision of Antibiotics A54145

A54145 is a family of antibacterial cyclic lipodepsipeptides structurally resembling daptomycin. Since its discovery in 1990, only the ambiguous structures of the methoxy-aspartic acid (MeO-Asp) and the hydroxy-asparagine (HO-Asn) have been reported. We have developed efficient routes to obtain the fully protected l-MeO-Asp and l-HO-Asn building blocks compatible with Fmoc-SPPS, and a total synthesis of A54145 that enabled us to establish its structure, consisting of l-3S-HO-Asn and l-3R-MeO-Asp, revising the wrongly proposed structure of l-3S-MeO-Asp.

Concise synthesis of all stereoisomers of β-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A

(Chemical Equation Presented) All stereoisomers of β-methoxytyrosine (β-OMeTyr), a stereo-undefined component of callipeltin A, were synthesized from L- and D-tyrosine. The stereochemistry of β-OMeTyr in callipeltin A was determined to be 2R,3R by an oxidative procedure and Marfey's analysis.

Complete stereochemistry of neamphamide A and absolute configuration of the β-methoxytyrosine residue in papuamide B

The absolute stereochemistry of the three unresolved structural components in neamphamide A (1) was determined to be (R)-β-methoxy-L-tyrosine, (2R,3A,4S)-4-amino-7-guanidino-2,3-dihydroxy-heptanoic acid, and (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid. Stereochemical assignments were made by chemical degradation of 1, derivatization of the resulting products, and then spectroscopic and chromatographic comparison of the derivatives with synthetically prepared standards. Using the same analytical protocol developed for 1, the β-methoxytyrosine residue in papuamide B (2) was found to be (R)-β-methoxy-D-tyrosine. This represents a rare example of divergent stereochemistry in an unusual amino acid residue that is present in two closely related classes of peptides.

Syntheses of optically pure β-hydroxyaspartate derivatives as glutamate transporter blockers

DL-threo-β-Benzyloxyaspartate (DL-TBOA) is a non-transportable blocker of the glutamate transporters that serves as an indispensable tool for the investigation of the physiological roles of the transporters. To examine the precise interaction between a blocker and the transporters, we synthesized the optically pure isomers (L- and D-TBOA) and its erythro-isomers. L-TBOA is the most potent blocker for the human excitatory amino acid transporters (EAAT1-3), while D-TBOA revealed a difference in the pharmacophores between EAAT1 and EAAT3. We also synthesized the substituent variants (methyl or naphthylmethyl derivatives) of L-TBOA. The results obtained here suggest that bulky substituents are crucial for non-transportable blockers. (C) 2000 Elsevier Science Ltd.